Modern bioorganic chemistry - an extensive area of \u200b\u200bknowledge, the foundation of many medical disciplines and primarily biochemistry, molecular biology, genomics, proteomics and

bioinformatics, immunology, pharmacology.

The program is based on a systematic approach to the construction of the entire course on a single theoretical

basis based on the ideas about the electronic and spatial structure of organic

compounds and mechanisms of their chemical transformations. The material is presented in the form of 5 sections, the most important of which: "Theoretical foundations of the structure organic compounds and factors defining their reactivity "," biologically important classes of organic compounds "and" biopolymers and their structural components. Lipids"

The program is aimed at profile teaching bio organic chemistry In a medical university, therefore discipline named "Bioorganic chemistry in medicine". Profiling to teach bioorganic chemistry to consideration of the historical relationship of the development of medicine and chemistry, including organic, increased attention to the classes of biologically important organic compounds (heterofunctional compounds, heterocycles, carbohydrates, amino acids and proteins, nucleic acids, lipids) as well as biologically important reactions of these compound classes ). A separate section of the Program is devoted to considering the pharmacological properties of some classes of organic compounds and the chemical nature of some classes of medicines.

Given the important role of "oxidative stress diseases" in the structure of the incidence of a modern person in the program, special attention is given to the reactions of free radical oxidation, the detection of finite products of free radical oxidation of lipids in laboratory diagnostics, natural antioxidants and antioxidant drugs. The program provides for consideration environmental problems, namely, the nature of xenobiotics and the mechanisms of their toxic action on living organisms.

1. Objective and learning tasks.

1.1. The purpose of training is the subject of bioorganic chemistry in medicine: to form an understanding of the role of bioorganic chemistry as a foundation of modern biology, theoretical basis for explaining the biological effects of bioorganic compounds, mechanisms of action of drugs and creating new drugs. To lay knowledge of the relationship of the structure, chemical properties and biological activity of the most important classes of bioorganic compounds, teach the applied knowledge gained when studying subsequent disciplines and in professional activities.

1.2. Supports of training of bioorganic chemistry:

1. Formation of knowledge of the structure, properties and mechanisms of reactions of the most important classes of bioorganic compounds caused by their medical and biological significance.

2. Formation of ideas about the electronic and spatial structure of organic compounds as a basis for explaining their chemical properties and biological activity.

3. Formation of skills and practical skills:

classify bioorganic compounds on the structure of carbon skeleton and functional groups;

use the rules of the chemical nomenclature to indicate the names of metabolites, medicines, xenobiotics;

determine reaction centers in molecules;

be able to spend qualitative reactionshaving clinical and laboratory value.

2. Place of discipline in the PCO structure:

Discipline "Bioorganic chemistry" is an integral part of the discipline "Chemistry", which refers to the mathematical, natural-scientific cycle of disciplines.

The main knowledge necessary for studying disciplines is formed in the cycle of mathematical, natural-scientific disciplines: physics, mathematics; Medical informatics; chemistry; biology; Anatomy, histology, embryology, cytology; Normal physiology; Microbiology, virology.

It is preceding for studying disciplines:

biochemistry;

pharmacology;

microbiology, virology;

immunology;

professional disciplines.

Parallel disciplines that provide interdisciplinary bonds in the framework of the framework of the curriculum:

chemistry, physics, biology, 3. List of disciplines and the assimilation of which students are necessary for studying bioorganic chemistry.

General chemistry. The structure of the atom, the nature of chemical bond, types of links, chemical classes, types of reactions, catalysis, medium reaction in aqueous solutions.

Organic chemistry. Classes of organic substances, nomenclature of organic compounds, configuration of carbon atom, polarization of atomic orbitals, sigma and pi- communication. Genetic communications Classes of organic compounds. The reactivity of different classes of organic compounds.

Physics. The structure of the atom. Optics - ultraviolet, visible and infrared spectrum areas.

The interaction of light with a substance is transmitting, absorption, reflection, scattering. Polarized light.

Biology. Genetic code. Chemical bases of heredity and variability.

Latin language. Mastering terminology.

Foreign language. The ability to work with foreign literature.

4. Sections of discipline and interdisciplinary connections with provided (subsequent)disciplines No. sections of this discipline necessary for studying the provisions provided No. The name provided by P / P (subsequent) disciplines (subsequent) disciplines 1 2 3 4 5 1 Chemistry + + + + + biology + - - + + biochemistry + + + + + + 4 Microbiology, virology + + - + + + 5 Immunology + - - - + Pharmacology + + - + + + 7 hygiene + - + + + professional disciplines + - - + + + 5. Requirements for the level of learning the content of the discipline Disciplines "Bioorganic Chemistry" provides for a number of targeted problem problems, as a result of which students need to be formed certain components, knowledge, skills, certain practical skills should appear.

5.1. The student must possess:

5.1.1. Communication competences:

the ability and willingness to analyze socially significant problems and processes, to use the methods of humanitarian, natural science, biomedical and clinical sciences in various types of professional and social activities in practice (OK-1);

5.1.2. Professional competencies (PC):

ability and readiness to apply the main methods, methods and means of obtaining, storing, processing scientific and professional information; receive information from various sources, including using modern computer tools, network technologies, databases and ability and willingness to work with scientific literature, analyze information, lead a search, turning read to a means to solve professional tasks (allocate the main provisions, effect from them and suggestions);

ability and readiness to participate in the formulation of scientific tasks and their experimental implementation (PC-2, PC-3, PK-5, PC-7).

5.2. The student should know:

Principles of classification, nomenclature and isomerism of organic compounds.

The fundamental basics of theoretical organic chemistry, which are the basis for studying the structure and reactivity of organic compounds.

The spatial and electron structure of organic molecules and chemical transformations of substances that are participants in the processes of life, in direct communication with their biological structure, chemical properties and the biological role of the basic classes of biologically important organic compounds.

5.3. The student must be able to:

Classify organic compounds on the structure of the carbon skeleton and by nature of functional groups.

Make formulas by names and call structural formula Typical representatives of biologically important substances and medicines.

Select functional groups, acidic and basic centers, conjugate and aromatic fragments in molecules to determine the chemical behavior of organic compounds.

Predict the direction and result of the chemical transformations of organic compounds.

5.4. The student must possess:

Skills independent work with educational, scientific and reference literature; Search and make generalizing conclusions.

Have chemical dishes handling skills.

Have the skills of safe work in a chemical laboratory and the ability to handle caustic, poisonous, volatile organic compounds, working with burners, alcohol and electric heating devices.

5.5. Knowledge Control Forms 5.5.1. Current control:

Diagnostic control of mastering material. It is carried out periodically mainly to control the knowledge of the formula.

Training computer control at every occupation.

Test tasks requiring skills to analyze and summarize (see Appendix).

Planned colloquiums upon completion of the study of large sections of the program (see Appendix).

5.5.2 Total control:

Offset (held in two stages):

C.2 - Mathematical, natural science and medical and biological Total labor intensity:

2 Classification, Nomenclature and Classification and Classification Signs of Organic Modern Physico Compounds: The structure of the carbon skeleton and the nature of the functional group.

chemical methods Functional groups, organic radicals. Biologically important studies of bioorganic classes of organic compounds: alcohols, phenols, thiols, ethers, sulphides, aldehyde compounds, ketones, carboxylic acids and their derivatives, sulfonic acids.

the nomenclature of the Jew. Varieties of international nomenclature replacement and radical-functional nomenclature. Meaning of knowledge 3 Theoretical bases of the structure of organic compounds and the theory of structure of organic compounds AM Butlerova. The main factors determining their provisions. Structural formulas. The nature of the carbon atom on the position in the reaction capacity. chains. Isomeria as a specific phenomenon of organic chemistry. Types of stereoisomeria.

The chirality of organic compound molecules as a cause of optical isomerism. Stereoisomeria of molecules with one center of chirality (enantiomerium). Optical activity. Glycerin aldehyde as a configuration standard. Projection formulas Fisher. D and L-system of stereochemical nomenclature. Representations of R, s-nomenclature.

Stereoisomeria molecules with two or more centers of chirality: enantiomeria and diastereomeria.

Stereoisomeria in a series of double-connected compounds (pidiasteromeria). Cis- and trans-isomers. Stereoisomeria and biological activity of organic compounds.

The mutual influence of atoms: the causes of the occurrence, types and methods of its transfer in organic compounds molecules.

Conjugation. Coupling in open circuits (PI). Conjugated connections. Dien structures in biologically important compounds: 1,3-diene (butadiene), polyenes, alpha, beta-sunsited carbonyl compounds, carboxyl group. Conjugation as a system stabilization factor. Energy of pairing. Coupling in the arenas (PI) and in heterocycles (P-PI).

Aromaticity. Aromatic criteria. The flavoring of benzoid (benzene, naphthalene, anthracene, phenantrene) and heterocyclic (furan, thiophene, pyrrol, imidazole, pyridine, pyrimidine, purine) compounds. Wide prevalence of conjugate structures in biologically important molecules (Porphin, Gem, etc.).

Polarization of bonds and electronic effects (inductive and mesomeric) as a reason for the uneven distribution of electron density in the molecule. Substituents - electroneons and electron acceptors.

The most important substituents and their electronic effects. Electronic effects of substituents and the reactivity of molecules. Rule of orientation in the benzene ring, substituents I and II of the genus.

Acidness and basicity of organic compounds.

Acidness and basicity of neutral organic compound molecules with hydrogen-containing functional groups (amines, alcohols, thiols, phenols, carboxylic acids). Acids and bases according to Brenssululouuri and Lewis. Conjugated pairs of acids and bases. Acidity and stability of anion. Quantitative assessment of the acidity of organic compounds in terms of ka and rock values.

Acidity of various classes of organic compounds. Factors that determine the acidity of organic compounds: electronegability of the non-metal atom (C-H, N-H, and O-H acid); polarizability of the nonmetal atom (alcohols and thiols, thiol poisons); The nature of the radical (alcohols, phenols, carboxylic acids).

The basicity of organic compounds. N-bases (heterocycles) and Pyension (alkenes, alkandeines, arena). Factors that determine the basicity of organic compounds: electronegate heteroatom (o- and notice); polarizability of the non-metal atom (o- and s-base); The nature of the radical (aliphatic and aromatic amines).

The value of the acid-base properties of neutral organic molecules for their reactivity and biological activity.

Hydrogen bond as a specific manifestation of acid-base properties. The general patterns of the reactivity of organic compounds as the chemical basis of their biological functioning.

Mechanisms of reactions of organic compounds.

Classification of the reactions of organic compounds according to the result Replacement, attachment, elimination, rearrangement, oxidizing agent and mechanism - radical, ionic (electrophyl, nucleophilic). Types of covalent bonding in organic compounds and particles formed: Gomolitic gap (free radicals) and heterolytic gap (carboations and carboanions).

The electronic and spatial structure of these particles and the factors resulting in their relative stability.

Homolytic reactions of radical substitution in alkanes with participation Sn connections SP 3-hybridized carbon atom. Reactions of free radical oxidation in a living cell. Active (radical) forms of oxygen. Antioxidants. Biological significance.

Electrophyl addition reactions (AE): heterolithic reactions involving a PI-communication. Mechanism of halogenation and ethylene hydration reactions. Acid catalysis. The influence of static and dynamic factors on the region selectivity of reactions. Features of the reactions of the addition of hydrogen-containing substances to pi-bonds in asymmetric alkenes. Markovnikov rule. Features of electrophile joining to conjugate systems.

Electful substitution reactions (SE): heterolithic reactions involving an aromatic system. The mechanism of reactions of electrophile substitution in the arenas. Sigma complexes. The reactions of alkylation, acylation, dense, sulfonia, halogenation of arena. Rule of orientation.

Deputy I-go and II. Features of electrophilic reactions in heterocycles. The orienting effect of heteroatoms.

The reactions of nucleophilic substitution (SN) at a SP3-hybridized carbon atom: heterolithic reactions caused by the polarization of the sigma bondage of carbon-heteroatom (halogen derivatives, alcohols). Effect of electronic and spatial factors on the reaction capacity of compounds in nucleophilic substitution reactions.

Hydrolysis reaction halogen derivatives. Alkylation reactions of alcohols, phenols, thiols, sulphides, ammonia and amines. The role of acid catalysis in the nucleophilic substitution of the hydroxyl group.

Disamination of compounds with primary amino group. The biological role of alkylation reactions.

Elimination reactions (dehydrogalogenation, dehydration).

Elevated CH-acidity as the cause of elimination reactions accompanying nucleophilic substitution in a SP3-hybridized carbon atom.

The reactions of nucleophilic addition (AN): heterolithic reactions with the participation of carbon-oxygen pi-bond (aldehyde, ketones). Classes of carbonyl compounds. Representatives. Obtaining aldehydes, ketones, carboxylic acids. The structure and reactivity of the carbonyl group. The influence of electronic and spatial factors. The mechanism of reactions AN: the role of protonation in increasing the reaction capacity of carbonyl. Biologically important reactions of aldehyd and ketones Hydrogenation, oxidation-reduction of aldehydes (dismantia reaction), oxidation of aldehydes, the formation of cyanhydrines, hydration, the formation of semi-acetals, imine. Aldol deal reactions. Biological significance.

The reactions of nucleophilic substitution in the SP2 hybridized carbon atom (carboxylic acids and their functional derivatives).

The mechanism of nucleophilic substitution reactions (Sn) in SP2Hybridized carbon atom. The acylation reactions - the formation of anhydrides, esters, complex thioethers, amides, and inverse the reactions of hydrolysis. The biological role of acylation reactions. Acid properties of carboxylic acids on the ON group.

Reactions of oxidation and restoration of organic compounds.

Redox reactions, electronic mechanism.

The degree of oxidation of carbon atoms in organic compounds. Oxidation of primary, secondary and tertiary carbon atoms. Oxidation of various classes of organic compounds. Ways to utilize oxygen in a cell.

Energy oxidation. Oxidase reactions. The oxidation of organic substances is the main source of energy for chemotrofs. Plastic oxidation.

4 Biologically important classes of organic compounds Multiatomic alcohols: ethylene glycol, glycerin, inosit. Hydroxy acid formation: classification, nomenclature, representatives of dairy, betaonessyllane, gammaoxymal, apple, wine, lemon, restorative amination, reaminting and decarboxylation.

Amino acids: classification, representatives of beta and gammaisomers aminopropane, gammaamic oil, epsilonamicapron. Salicylic acid reaction and its derivatives (acetylsalicylic acid antipyretic, anti-inflammatory and antipers, enteroseptol and 5-nct. The isoquinoline core as the basis of alkaloids of spasmolytic (papaverine) and analgesics (morphine). Derivatives of acridine disinfectants.

ksanthina derivatives - caffeine, theobromin and theophiline, indole derivatives reserpine, Strichnin, Pilocarpine, chinoline derivatives - chinin, isoquinoline morphine and papaverine.

cefalosproines are trefalospioran derivatives, tetracycles naphtacene derivatives, streptomycins - amyloglycosides. Semi-synthetic 5 biopolymers and their structural components. Lipids. Definition. Classification. Functions.

Cyclo-oxotomeria. Mutarization. Deroxachara monosaccharide derivatives (deoxyribosis) and amino-amahar (glucosamine, galactosamine).

Oligosaccharides. Disaccharides: maltose, lactose, sucrose. Structure. Firecosium connection. Restoring properties. Hydrolysis. Biological (the path of decomposition of amino acids); Radical reactions - hydroxylation (formation of amino acid hydroxy derivatives). The formation of peptide communications.

Peptides. Definition. The structure of the peptide group. Functions.

Biologically active peptides: glutathione, oxytocin, vasopressin, glucagon, neuropeptides, kinin peptides, immunoactive peptides (thymbosin), inflammation peptides (dipxen). Concept of cytokines. Antibiotic peptides (gramicidine, actinomycin D, cyclosporin A). Peptides-toxins. The relationship of biological effects of peptides with certain amino acid residues.

Proteins. Definition. Functions. Levels of protein structure. The primary structure is the sequence of amino acids. Research methods. Partial and complete protein hydrolysis. The value of determining the primary structure of proteins.

Directional place-specific mutagenesis as a method for studying the relationship of the functional activity of proteins with primary structure. Congenital disorders of the primary structure of proteins - point mutations. Secondary structure and its types (alpha spiral, beta structure). Tertiary structure.

Denature. The concept of active centers. Quaternary structure of oligomeric proteins. Cooperative properties. Simple and complex glycoprotein proteins, lipoproteins, nucleoproteins, phosphoproproids, metalloproteides, chromoproteins.

Nitrogen bases, nucleosides, nucleotides and nucleic acids.

Determination of the concepts of a nitrogen base, nucleoside, nucleotide and nucleic acid. Purine (adenine and guanine) and pyrimidine (uracil, thymine, cytosine) nitrogenous bases. Aromatic properties. Resistance to oxidative decay as a basis for the fulfillment of the biological role.

Laktim is a lactam tautomeria. Minor nitrogen bases (hypoxanthine, 3-N-methyluracyl, etc.). Derivatives of nitrogen bases - antimetabolites (5-fluorouracil, 6-mercaptopurine).

Nucleosides. Definition. The formation of a glycoside relationship between a nitrogen base and pentose. Hydrolysis of nucleosides. Nucleosydimatimetabolites (adenine arabinoside).

Nucleotides. Definition. Structure. The formation of phosphoeter communication with esterification of C5 hydroxyl pentose phosphoric acid. Hydrolysis of nucleotides. Nucleotides-macroeergi (nucleosidepolyphosphates - ADP, ATP, etc.). Nucleotides-coefficers (above +, phad), structure, role of vitamins B5 and B2.

Nucleic acids - RNA and DNA. Definition. Nucleotide composition of RNA and DNA. Primary structure. Phosphodieter communication. Hydrolysis of nucleic acids. Defining the concepts of triplet (codon), gene (cystroon), genetic code (genome). International project "Man's Genome".

Secondary DNA structure. The role of hydrogen bonds in the formation of the secondary structure. Complete pairs of nitrogen bases. Tertiary DNA structure. Changes in the structure of nucleic acids under the influence of chemicals. The concept of substances mutagen.

Lipids. Definition, classification. Washed and unlimited lipids.

Natural higher fatty acids - lipid components. The most important representatives: palmitic, stearinovaya, oleic, linolevial, linolenic, arachidon, eikosopentaena, approxocent (vitamin F).

Neutral lipids. Acilglycerin - Natural Fats, Oils, Wax.

Artificial food hydrins. The biological role of acylglycerin.

Phospholipids. Phosphatidic acids. Phosphatidylcholines, phosphatidatehanolamines and phosphatidylserine. Structure. Participation in the formation of biological membranes. Lipid peroxidation in cell membranes.

Sphingolipid. Sphinosin and Sphingomyelina. Glycolipids (cerebroids, sulfatis and gangliosides).

Unlimited lipids. Terpene. Mono- and bicyclic terpinas 6 Pharmacological properties The pharmacological properties of some classes of mono-poly and some classes of heterofunctional compounds (halogenerates, alcohols, hydroxy- and organic compounds. Oxocuslots, benzene derivatives, heterorocycles, alkaloids.). Chemical chemical nature of some nature of anti-inflammatory, analgesics, antiseptics and drug classes. Antibiotics.

6.3. Sections of disciplines and types of classes 1. Introduction to the subject. Classification, nomenclature and studies of bioorganic compounds 2. Theoretical foundations of the structure of organic reactivity.

3. Biologically important classes of organic 5 pharmacological properties of some classes of organic compounds. The chemical nature of some classes of drugs of the L ( PZ - practical classes; LR - laboratory work; C - seminars; SRS - independent work of students;

6.4 Thematic plan of lectures on discipline 1 1 Introduction to the subject. The history of the development of bioorganic chemistry, the value for 3 2 the theory of the structure of organic compounds A.M. Butlerova. Isomerius as 4 2 Mutual influence of atoms: causes of occurrence, types and methods of its transmission in 7 1.2 test work on the sections "Classification, nomenclature and modern physicochemical methods of study of bioorganic compounds" and "Theoretical foundations of the structure of organic compounds and factors defining their reaction 15 5 Pharmacological properties of some classes of organic compounds. Chemical 19 4 14 Detection of insoluble calcium salts of higher carboxylices 1 1 Introduction to the subject. Classification and work with recommended literature.

nomenclature of bioorganic compounds. Performing a written task for 3 2 Mutual influence of atoms in molecules Working with recommended literature.

4 2 Acidness and basicity of organic work with recommended literature.

5 2 Mechanisms of organic reactions work with recommended literature.

6 2 Oxidation and restoration of organic work with recommended literature.

7 1.2 Examination on sections Work with recommended literature. * Modern physico-chemical methods offered topics, conducting a study of bioorganic compounds "of information retrieval in various organic compounds and factors, internet and work with English-speaking bases 8 3 heterofunctional bioorganic work with recommended literature.

9 3 biologically important heterocycles. Work with recommended literature.

10 3 Vitamins (laboratory work). Work with recommended literature.

12 4 alpha amino acids, peptides and proteins. Work with recommended literature.

13 4 Nitrogen bases, nucleosides, work with recommended literature.

nucleotides and nucleic acids. Performing a written task on writing 15 5 Pharmacological properties of some work with recommended literature.

classes of organic compounds. Performing a written task on writing the chemical nature of some classes chemical formulas Some medicinal * - tasks for the selection of a student.

organic compounds.

organic molecules.

organic molecules.

organic compounds.

organic compounds.

connections. Stereoisomeria.

some classes of medicines.

For the semester, the student can gain the maximum 65 points in practical classes.

At one practical lesson, the student can maximize 4.3 points. This number is consisted of points gained for visiting classes (0.6 points), performing a task for extracurricular independent work (1.0 points), laboratory work (0.4 points) and points accrued for oral response and test task (from 1 3 to 2.3 points). Points for visiting the classes, the fulfillment of the task of extracurricular independent work and laboratory work is charged according to the principle "Yes" - "No". Points for the oral response and test task are accrued differentiated from 1.3 to 2.3 points in cases of positive responses: 0-1.29 points corresponds to the evaluation "unsatisfactory", 1.3-1.59 - "satisfactory", 1.6 -1.99 - "Good", 2.0-2.3 - "excellent." In the test work, the student can maximize 5.0 points: a visit to the occupation of 0.6 points and the oral response of 2.0-4.4 points.

For admission to test, the student must score at least 45 points, while the current student performance is assessed as follows: 65-75 points - "excellent", 54-64 points - "Good", 45-53 points - "satisfactory", less than 45 Points are unsatisfactory. If the student is gaining from 65 to 75 points ("excellent" result), then it is freed from the credit and receives the "Offset" mark in the test book automatically, gaining up for offset 25 points.

At the standings, the student can dial 25 points as possible: 0-15.9 points corresponds to the evaluation "unsatisfactory", 16-17.5 - "satisfactory", 17.6-21.2 - "Good", 21.3-25 - " excellent".

Distribution of premium points (only up to 10 points per semester) 1. Visit to the lecture - 0.4 points (100% visiting lectures - 6.4 points per semester);

2. Participation in UIRS to 3 points, including:

writing an essay on the topic offered - 0.3 points;

preparation of the report and multimedia presentation for the final educational and theoretical conference 3. Participation in Nirs - up to 5 points, including:

visit the meeting of the student scientific circle at the Department - 0.3 points;

preparation of the report to the meeting of the student scientific circle - 0.5 points;

speech with a report at the university student scientific conference - 1 point;

speech with a report at the regional, All-Russian and International Student Scientific Conference - 3 points;

publication in collections of student scientific conferences - 2 points;

publication in a peer-reviewed scientific journal - 5 points;

4. Participation B. educational work At the pulpit of up to 3 points, including:

participation in the organization of the activities held by the Department of Events for Educational Work in the extracurricular time - 2 points for one event;

a visit to the activities held by the Department of Events for Educational Work in the extracurricular time - 1 point for one event;

The distribution of penalty points (only up to 10 points per semester) 1. The absence on the lecture on a disrespectful reason, 0.66-0.67 points (0% of visits to lectures - 10 points for if the student missed an exercise for a good reason, he has the right to work out To enhance your current rating.

If the missing is disrespectful - the student must work out the occupation and obtain an estimate with a downstream coefficient of 0.8.

If the student is freed from the physical presence in class (by order of the Academy), then he is charged maximum pointsIf a task is made on extracurricular independent work.

6. Educational and methodical and informational support of discipline 1. N.A.Tyukavkina, Yu.I. Baukov, S.E. Zuraban. Bioorganic chemistry. M.: Drop, 2009.

2. Tubavkina N.A., Baukov Yu.I. Bioorganic chemistry. M.: Drop, 2005.

1. Ovchiknikov Yu.A. Bioorganic chemistry. M.: Enlightenment, 1987.

2. Rails A., Smith K., Ward R. Basics of organic chemistry. M.: Mir, 1983.

3. Shcherbak I.G. Biological chemistry. Tutorial for medical universities. S.-P. Publishing house SPBGMU, 2005.

4. Berezov T.T., Korovkin B.F. Biological chemistry. M.: Medicine, 2004.

5. Berezov T.T., Korovkin B.F. Biological chemistry. M.: Medicine, Additions V.V., Ryabtseva E.G. Biochemical organization of cell membranes (tutorial for students of pharmaceutical faculties of medical universities). Khabarovsk, DVGMU. 2001

7. SOROSE EDUCATIONAL JOURNAL, 1996-2001.

8. Guide to laboratory classes on bioorganic chemistry. Edited by N.A. Dukkavina, M.:

Medicine, 7.3 Educational materials prepared by the Department 1. Methodical development of practical training in bioorganic chemistry for students.

2. Methodological developments of independent extracurricular work of students.

3. Borodin E.A., Borodina G.P. Biochemical diagnosis (physiological role and diagnostic value of biochemical indicators of blood and urine). Tutorial Edition 4. Blagoveshchensk, 2010.

4. Borodina G.P., Borodin E.A. Biochemical diagnosis (physiological role and diagnostic value of biochemical indicators of blood and urine). Electronic study guide. Blagoveshchensk, 2007.

5. Tasks for computer testing of knowledge of students on bioorganic chemistry (Cost. Borodin E.A., Doroshenko G.K., Egorshina E.V.) Blagoveshchensk, 2003.

6. Test tasks for bioorganic chemistry to the exam on bioorganic chemistry for students of the medical faculty of medical universities. Toolkit. (Sost. Borodin E.A., Doroshenko G.K.). Blagoveshchensk, 2002.

7. Test tasks for bioorganic chemistry to practical exercises on bioorganic chemistry for students of the medical faculty. Toolkit. (Sost. Borodin E.A., Doroshenko G.K.). Blagoveshchensk, 2002.

8. Vitamins. Toolkit. (Sost. Erhorshina E.V.). Blagoveshchensk, 2001.

8.5 Ensuring discipline equipment and educational materials 1 Chemical dishes:

Glassware:

1.1 Test tubes Chemical 5000 Chemical experiments and analyzes in practical classes, UIRS, 1.2 Test tubes Centrifuge 2000 Chemical experiments and analyzes in practical classes, UIRS, 1.3 Glass sticks 100 Chemical experiments and analyzes in practical training, UIRS, 1.4. Flasks of various volumes (for 200 chemical experiments and analyzes in practical classes, UIRS, 1.5 Bolshoi flasks - 0.5-2.0 30 Chemical experiments and analyzes in practical training, UIRS, 1.6 Chemical glasses of various 120 chemical experiments and analyzes on practical Classes, UIRS, 1.7 Chemical glasses of large 50 chemical experiments and analyzes in practical classes, UIRS, cooking workers 1.8 Flasks of various volumes of 2000 Chemical experiments and analyzes in practical training, UIRS, 1.9 Filtering funnels 200 Chemical experiments and analyzes in practical training, WERS , 1.10 Glassware Chemical experiments and analyzes in practical training, UIRS, chromatography, etc.).

1.11 Alcohol 30 Chemical experiments and analyzes in practical classes, UIRS, Porcelainware 1.12 Glassesmiscellaneous volume (0.2-30 Preparation of reagents on practical classes 1.13 Mortar with pestles Preparation of reagents for practical classes, chemical experiments and 1.15 cups for evaporation 20 Chemical experiments and analyzes in practical training, UIRS, measuring dishes:

1.16 Measuring flasks of various 100 Preparation of reagents for practical classes, chemical experiments 1.17 Measuring cylinders of various 40 preparation of reagents for practical classes, chemical experiments 1.18 Menzurics of various volumes 30 Preparation of reagents for practical classes, Chemical experiments 1.19 Pipettes measuring on 2000 Chemical experiments and analyzes in practical Classes, UIRS, micropipettes) 1.20 Mechanical automatic 15 Chemical experiments and analyzes in practical classes, UIRS, 1.21 Mechanical automatic 2 Chemical experiments and analyzes in practical training, UIRS, VARIATIVES 1.22 Dispensers 1.22 Electronic automatic 1 Chemical experiments and analyzes in practical exercises, UIRS, 1.23 Microfits of AC 5 Chemical experiments and analyzes in practical training, UIRS, 2 Technical equipment:

2.1 Tripods for test tubes 100 Chemical experiments and analyzes in practical training, UIRS, 2.2 Triples for pipettes 15 Chemical experiments and analyzes in practical training, UIRS, 2.3 Students Metal 15 Chemical experiments and analyzes in practical classes, WERS, Heating appliances:

2.4 Drying Cabinets 3 Drying Chemical Cookware from Glass, Conducting Chemical 2.5 Thermostats Air 2Thermostatting of the incubation mixture in determining 2.6 Thermostats Water 2 Thermostatting of the incubation mixture in determining 2.7 Power plants 3 Preparation of reagents on practical classes, chemical experiments and 2.8 refrigerators with freezing 5 Storage of chemicals, solutions and biological material for Chinar cameras, Biryusi, practical training , UIRS, NERS "Stinol"

2.9 storage cabinets 8 storage of chemicals chemicals 2.10 Metal safe 1 storage of poisonousreagents and ethanol 3 general purpose equipment:

3.1 Analytical damper 2 gravimetric analysis in practical classes, UIRS, NERS 3.6 Ultracentrifugu 1 Demonstration of the method of sedimentation analysis on practical (Germany) 3.8 Magnetic stirrers 2 Preparation of reagents for practical classes 3.9 DEFLINER DEVERATIVE DEE-1 OPERATION OF DISTENED WATER CREATE WATER 3.10 THERMOMETERS 10 Temperature control when conducting chemical analyzes at 3.11 Set of ranges 1 Measurement of density of solutions 4 Special purpose equipment:

4.1 Electrophoresis apparatus 1 Demonstration of the electrophoresis method of serum proteins by 4.2 Electrophoresis apparatus in 1 Demonstration of the separation of serum lipoproteins 4.3 Equipment for a column Demonstration of protein separation method using chromatography 4.4 Equipment for the demonstration of the TLC method for dividing lipids on practical chromatography in thin layer. Classes, NURS Measuring equipment:

Photoelectrocolorimeters:

4.8 Photometer "Solar" 1 Measurement of light absorption of painted solutions at 4.9 Spectrophotometer SF 16 1 Measurementlight absorption of solutions in visible and UV regions 4.10 Clinical spectrophotometer 1 Measurement of light absorption solutions in visible and UV areas "Schimadzu - CL-770" spectrum when using spectral definition methods 4.11 High-efficient 1 Demonstration of HPLC method (practical classes, UIRS, NERS) Liquid chromatograph "Milichrom - 4".

4.12 Polarimeter 1 Demonstration of optical activity of enantiomers, 4.13 Refractometer 1 Demonstrationrefractometric method of definition 4.14 pH meters 3 Preparation of buffer solutions, Demonstration of buffer 5 Projection equipment:

5.1 Multimedia Projector and 2 Demonstration multimedia presentations, photo and diametrorectors: demonstrationslides at lectures and practical classes 5.3 "Pereleng-semi-automatic" 5.6 The device for the demonstration is fixed behind the morphological training case. Demonstration of transparent films (Overhead) and illustrative material at lectures, during UIRS and NERS film projector.

6 Computing Technique:

6.1 Cathedral of 1 access to Internet educational resources (national and personal computers with international electronic databases in chemistry, biology and Internet access medicine) for teachers of the Department and Students in Educational and 6.2 Personal Computers 8 Creating Teachers of the Department of Printed and Email Ceads Didactic materials during educational and methodical work, 6.3 Computer class at 10 1 Programmed testing of students' knowledge on the landing places of practical training, during tests and exams (current, 7 Tutorials:

1. Peptide communications.

2. Regularity of the structure of the polypeptide chain.

3. Types of ties in the protein molecule.

4. Disulfide bond.

5. Specific specificity of proteins.

6. Secondary structure of proteins.

7. The tertiary structure of proteins.

8. Mioglobin and hemoglobin.

9. Hemoglobin and its derivatives.

10. Blood plasma lipoproteins.

11. Types of hyperlipidemias.

12. Electrophoresis of proteins on paper.

13. Scheme of protein biosynthesis.

14. Collagen and tropocoleggen.

15. Mozin and Aktin.

16. Avitamin RP (Pellagra).

17. Avitaminosis B1.

18. Avitamin S.

19. Avitaminosis A.

20. Avitaminosis D (Rakhit).

21. Prostaglandins are physiologically active derivatives of unsaturated fatty acids.

22. Nerokoxins formed from catechamins and indolamines.

23. Products are not enzymatic reactions of dopamine.

24. Neuropeptides.

25. Polyunsaturated fatty acids.

26. The interaction of liposomes with a cell membrane.

27. Free oxidation (distinction with tissue breathing).

28. PNCC of Omega 6 and Omega 3 families.

2 Sets of slides on various sections of the program 8.6 Interactive learning tools (Internet technologies), multimedia materials, electronic libraries and textbook, photo and video materials 1 Interactive learning tools (Internet technologies) 2 Multimedia materials Stonik V.A. (Tiboch DNC SB RAS) "Natural compounds - the basis of 5 Borodin E.A. (AGMA) "The human genome. Genomics, proteomics and author's presentation 6 Pivovarova E.N. (IZGC SO RAMS) "The role of regulation of gene expression author's presentation of a person."

3 Electronic libraries and textbooks:

2 MEDLINE. CD version of electronic databases for chemistry, biology and medicine.

3 Life Sciencies. CD version of electronic databases for chemistry and biology.

4 Cambridge Scientific Abstracts. CD version of electronic databases for chemistry and biology.

5 PubMed - electronic database of the National Institute of Health http://www.ncbi.nlm.nih.gov/pubmed/ Organic Chemistry. Digital library. (Sost. N.F. Tubavkin, A.I. Tailova) - M., 2005

Organic and general chemistry. Medicine. Lectures for students, course. (Electronic manual). M., 2005

4 Videos:

3 MES Tiboch DNC DVO RAS CD

5 photos - video footage:

Copyright photo and video footage. cafe. prof. E.A. Borodina about 1 universities UPSAL (Sweden), Granada (Spain), medical schools of Japan Universities (GGNIGAT, Osaka, Canadzava, Hiroshaki), IBMX RAMS, IFCHM MS of Russia, Tibooche DNC. DVO RAS.

8.1. Examples of test tasks of current control (with reference standards) to occupation №4 "Acidity and basenessorganic Molecules "

1. Select the characteristic signs of Brensted-Lowry acids:

1. The concentration in aqueous solutions of hydrogen ions 2. The concentration of hydroxide ion concentrations in aqueous solutions 3. The proton donors are 4. The protons with neutral molecules and ions - proton acceptors 5. The factors are influenced by affecting the acidity of organic molecules:

1.Electricatence of heteroatom 2. Heated heteroatoma 3. Radicel region. Observation of dissociation 5. Water solubility 3. Select the most listed compounds strong acids Brensteda:

1. The 2.amines 3. Snirts 4.Tiols. 5.Qarboxylic acids 4. Decide the characteristic features of organic compounds with base properties:

1. Proton acceptors 2. DONORS OF PROTONS 3. DISSOCIATION DISSOCIATION DOWN HYDROXY ions 4. Divociated 5. The main properties determine the reaction capacity 5. Select the weakest base from the above connections:

1.Mamiak 2.Metylamine 3.Phenylamine 4.Thylamine 5.Propylamine 8.2 Examples of current control situational problems (withequalons of responses) 1. Determine the general structure in conjunction:

Decision. The choice of the source structure in the structural formula of the organic compound is regulated in the reactive nomenclature of the Jewberry number of consistently applied rules (see Tutorial, 1.2.1).

Each subsequent rule applies only when the previous one does not allow you to make an unambiguous choice. Compound I contains aliphatic and alicyclic fragments. According to the first rule, the elemental characteristic group is selected as a general basis. Of the two components of the characteristic groups (it and NH,) the senior is the hydroxyl group. Therefore, the investigative will be the structure of cyclohexane, which is reflected in the title of this compound - 4-aminomethylcyclohexanol.

2. The basis of a number of biologically important compounds and drugs is a condensed heterocyclic purine system, including pyrimidine and imidazole kernels. What is explained by the increased resistance of Pyrin to oxidation?

Decision. Aromatic compounds possess large energy Coupling and thermodynamic stability. One of the manifestations of aromatic properties is resistance to oxidation, although "extern"

aromatic compounds have a high degree of unsaturation, which usually determines the tendency to oxidation. To respond to the task assigned to the condition, it is necessary to establish the pyrine affiliation to aromatic systems.

According to the determination of aromaticity, the necessary (but insufficient) condition for the occurrence of a conjugate closed system is the presence of a flat cyclic-silver molecule with a single electronic cloud. In the Purin molecule, all carbon and nitrogen atoms are in a state of SP2 hybridization, and therefore all asvia are lying in the same plane. Due to this, the orbital of all atoms included in the cycle are located perpendicular to the plane -cakely and parallel to each other, which creates conditions for their mutual overlap to form a single closed delocaliso-bathroom of the T-electronic system covering all cycle atoms (circular pairing).

The aromaticity is also determined by the number -Electrons, which must correspond to the formula 4/7 + 2, where P is a number of natural numbers O, 1, 2, 3, etc. (Hyukkel rule). Each carbon atom and pyridine nitrogen atoms in positions 1, 3 and 7 are added to the conjugate system by one P-electron, and the pyrrol atom of nitrogen at position 9 is a watered pair of electrons. The maturium conjugate system contains 10-electrons, which corresponds to the Hyukkel rule at n \u003d 2.

Thus, the pyrine molecule has an aromatic character and its resistance to oxidation is associated with it.

The presence in the cycle of purine heteroatoms leads to unevenness in the distribution of the electronic density. Pyridine nitrogen atoms exhibit electronically accurate character and reduce electron density on carbon atoms. In this regard, the oxidation of Purin, considered in the general case as the loss of electrons by an oxidizing compound, will be even more difficult compared to benzene.

8.3 Test assignments to a test (one option in full with reference standards) 1. Name organogenic elements:

7.Si 8.fe 9.CU 2. Suggest functional groups having a PI communication:

1. CARBOXY 2. AMINOGRUP 3. Hydroxyl 4. Sign 5.Karboonile 3. Learn the older functional group:

1.-C \u003d O 2.-SO3N 3.-CII 4.-SOM 5.-Oh 4. What class of organic compounds relate to lactic acid CH3-Sony-coxy, formed in tissues as a result of anaerobic glucose decay?

1. Curboxylic acids 2. Osic acids 3. Assoculotes 4. Baseline 5. Note by replacement nomenclature The substance that is the main energy fuel cell and having the following structure:

CH2-CH -CN -SN -SN -S \u003d O

I III I

Oh Oh Oh Oh n

1. 2,3,4,5,6-pentagidroxygexanal 2.6-Oxohexanentanol 1,2,3,4, 3. Glucose 4.Gexose 5.1,2,3,4,5-pentagidroxygexanal- 6. Tell the characteristic features of conjugate systems:

1. Evilization of electronic density of sigma- and pins 2. Support and low reactivity 3. Reityfulness and high reactivity 4. Conducting alternating sigma- and 5. -Pupplence pi-links are separated by -CH2 groups of 7. What compounds Characterist Pi-pi pairing:

1.Carotins and vitamin A 2.Pirrol 3.Pyridine 4.Porphyrine 5.Benzpires 8.Select the substituents of the type I focusing in ortho and pair positions:

1. Alkyls 2.- It is 3.- NH 4.- Soam 5.- SO3H 9. As the effect has a group in aliphatic alcohols:

1. Inductive inductive 2.-negative inductive 3. positive mesomeric 4. negative mesomeric 5.Type and the effect of the effect depend on the position of the group 10.Seate the radicals that have a negative mesomeric effect 1.Halogen 2. alkyl radicals 3. MineGroup 4.Hidroxigroup 5.Qarboxygroup 11.Select the characteristic features of Brenstened-Lowry acids:

1. The concentration in aqueous solutions of hydrogen ions 2. The concentration in aqueous solutions of hydroxide ions is performed 3. The names are neutral and ions - proton donors 4. The protons are neutral and ions - the proton acceptors 5. Therefore affect the reaction of the medium 12. For factors. affecting the acidity of organic molecules:

1.Electricatence of heteroatom 2. Heteroatoma 3. Radical drill. Justice to dissociation 5. Water solubility 13. Select the most strong acids of Brensteads from listed compounds:

1. Levels 2. Mine 3.Spirts 4.Tiols 5.Qarboxylic acids 14. Tell the characteristic features of organic compounds with the properties of the grounds:

1. Proton acceptors 2. DONOR protons 3. Dissociations give hydroxyl ions 4. Divociated 5. -Wound properties determine the reaction capacity 15. Select the weakest base from the above connections:

1.Mamiak 2.Metylamine 3.Phenylamine 4.Ethylamine 5.Propylamine 16. What signs are used to classify the reactions of organic compounds:

1. Mechanism of the chemical bonding 2.The results of the reaction 3. The number of molecules involved in the stage determining the speed of the entire process 4. The image of the attacking reagent connection 17.Select the active forms of oxygen:

1. Single oxygen 2. Peroxide biradical -o-osoupe oxide ion 4. Hydroxyl radical 5.Tractive molecular oxygen 18. Select the characteristic signs of electrophyl reagents:

1. Pacifics that carry partial or full positive charge 2. Causes with a homologous break of covalent coupling 3. Pachentians carrying an unpaired electron electron carrier, carrying partial or complete negative charge 5. Causes with a heterolithic covalent bond. 19.Select the compounds for which The reactions of electrophile substitution are characteristic:

1. Alkanes 2.Anes 3. Tools 4.Anomatic heterocycles.

1. Phaganoic activity of cells 2.Universal mechanism for the destruction of cell membranes 3. The presentation of cellular structures 4. Perform a decisive role in the development of many pathological processes 21. Select for which classes of organic compounds is characterized by nucleophilic replacement:

1. Snaps 2. The 4.Galogeneous hydrocarbons 4.Tioles 5.Lehydes 22. In which sequence reduces the reactivity of substrates in nucleophilic replacement reactions:

1. Halmetrogen derivatives of alcohol amines 2.amine alcohols Halogene derivatives of hydrocarbons 3. Amina halogen production hydrocarbons 4.Galogeneous hydrocarbons Amina alcohol 23.Select polymatomic alcohi from listed compounds:

1. ethanol 2.Thylen glycol 3. Glycerin 4.xilite 5.Sorbitates 24.Select characteristic of this reaction:

CH3-CH2ON --- CH2 \u003d CH2 + H2O 1. Reactivity of elimination 2. Reacting of intramolecular dehydration 3.The presence in the presence of mineral acids when heated 4.Things under normal conditions 5. Reactivity of the intermolecular dehydration 25. What properties appear when administered to the organic molecule Chlorine substances:

1. Narcotic properties 2. Lacking (tear) 3.Acteptic properties 26. Select reactions characteristic of SP2-hybridized carbon atom in oxo compounds:

1.Nochlorophilic addition 2.Nochelophilic substitution 3.Electrophilic connection 4.Gomolytic reactions 5. Motterolytic reactions 27. In which sequence, the ease of the nucleophilic attack of carbonyl compounds decreases:

1. Aldeehydical-chiderhydrideyeticiamidisols of carboxylic acids 2. Butonaldecarboxylic acids 3. Yungidcarboxylic acids 28. Directly characteristic of this reaction:

1. Complete reaction to aldehyde 2.aldehyde - reducing agent, silver oxide (I) - oxidizing agent 3.Aldehyde - oxidizing agent, silver oxide (I) - reducing agent 4. Oxidation-reducing reaction 5.Things in an alkaline medium 6. Cauctees for ketones 29 What from the above carbonyl compounds are subject to decarboxylation with the formation of biogenic amines?

1. CARBONICICICICS 2. SAMINISTURES 3. SOCIATURES 4. Oxyxylotes 5.Benzoic acid 30. How acidic properties are changed in the homologous row of carboxylic acids:

1. Increase 2. Dimensions 3. It is changed 31. Whats from the proposed compound classes refer to heterofunctional:

1. Oncexic acids 2. Sociality 3.Inhibries 4.Inoxylots 5.Dicarboxylic acids 32.k oxyc acids include:

1.Limonaya 2.Masyl and acetate 4.Pillinginograde 5.Yube 33.Select medicines - Salicylic acid derivatives:

1.Parazetomol 2.Fenacetin 3. Sulfanimamides 4.Aspirin 5.Pask 34.Select medicines - derivatives of p-aminophenol:

1.Parazetomol 2.Phenacetin 3. Sulfanimamides 4.Aspirin 5.Pask 35.Select medicines - sulfanyl acid derivatives:

1.Parazetomol 2.Fenacetin 3. Sulfanimamides 4.Aspirin 5.Pask 36.Select the main provisions of AM Butler's theory:

1. Carbonautomas are connected by simple and multiple bonds 2. Carbon in organic compounds of four-tape 3. Functional group determines the properties of the substance of the carbon. The carbon matters form open and closed cycles 5. In the organic compounds, carbon is in restored form 37.Work isomers refer to spatial:

1. Drug 2. The location of multiple bonds of 3.Functional groups 4. Design 5. Configuration 38.Select what is characteristic of the concept of "conformation":

1. The possibility of rotation around one or more sigma of bonds 2. Conforters is an isomer 3. By changing the sequence of links. 4. By changing the spatial location of the substituents 5. By changing the electronic structure 39.Seate the similarity between enantiomers and diastereomers:

1. Regarding the same physicochemical properties. 2. Delive to rotate the plane of the polarization of light 3. It is capable of rotating the plane of the polarization of light 4. The existence of a center of chirality 40. Select the similarities between the configuration and conformational isomeria:

1. Insometer is associated with different positions in the space of atoms and groups of atoms 2. The system is separated by the rotation of atoms or groups of atoms around the sigma coupling. 3. Resomery is due to the presence in the molecule of the center of chirality 4. Isomeria due to the different location of the substituents relative to the PI plane.

41. Name the heteroatoms included in biologically important heterocycles:

1.Azot 2. Forosphorus 3. Callery 5.Cyclood 42. Here, a 5-membered heterocycle, which is part of the porphyrins:

1.Pirrolidine 2. Iimidazole 3.Pirrol 4.Pizole 5.Furane 43.An a heterocycle with one heteroatom is part of nicotinic acid:

1.Purine 2.Piridin 3.Pyrrol 4.Pyridin 5.Pirimidine 44. Name the final poirin oxidation product in the body:

1.Gipoxanthine 2.xanthin 3.Moisy acid 45.Close opium alkaloids:

1.Stricine 2.Papalerin 4. Morphin 5. Racing 6.Hinin 6. What oxidation reactions are characteristic of the human body:

1. Dehydrification 2. Electron Oxygen Connection 3. Halogens 4. Digitalize Halogens 5. Recovery with potassium permanganate, nitric and chlorine acids 47. And the degree of oxidation of carbon atom in organic compounds is determined:

1. Its connections with atoms of elements, more electronegative than hydrogen 2. His links with oxygen atoms 3. Its connections with hydrogen atoms 48. What compounds are formed when the primary carbon atom is formed?

1. Purchase alcohol 2.Verical alcohol 3.aldehyde 4.Ukton 5.Qarboxylic acid 49. Directly characteristic of oxidase reactions:

1. Cycelodine is restored to the water 2. Cyclood is turned on into the composition of the oxidated molecule 3. Calculation is oxidized to oxidation of hydrogen cleaved from the substrate 4. Recovery have an energy value 5. Recovery have a plastic value 50.What from the proposed substrates oxidizes in the cell easier and why?

1. Glucose 2. Silent acid 3. The partially oxidized carbon atoms 4. Suitable completely hydrogenated carbon atoms 51. Select aldosis:

1. Glucose 2.Rebosis of 3.Fructose 4. Galatosis 5. Select the spare forms of carbohydrates in a living organism:

1. Racket 2. Account 3. Glylogen 4.Galuric acid 5.Share 53. Select the most common monosaccharides in nature:

1.Tripes 2. 3.Tentose 4. Gexose 5.Geptosis 54.Select Aminosahara:

1. Beta-robosis 2. Glucosamine 3. Galaktoosamine 4. Aacetylgalactosamine 5. Select the oxidation products of monoshares:

1. Glucoso-6-phosphate 2. Gliding (Aldon) Acids 3. Glikuronic (URON) Acid 4. Glycosides 5. FIRS 56.Select disaccharides:

1. Maltosis 2. Racket 3. Glylogen 4.Shairoz 5.Lotosis 57.Select homopolysaccharides:

1. Stacked 2. Saleloose 3. Glylogen 4. Detail 5. Lotosis 58. Select which monosachara is formed during lactose hydrolysis:

1. Beta-D- Galactosis 2. Falph-Dzhalucosis 3. Falph-Dutoff 4. Falifa-D-galactose 5. Falifa-Dzoxiribosis 59. Select what is characteristic of cellulose:

1. The standard, vegetable polysaccharide 2.structural unit is the beta-diablication 3. Overcome for normal nutrition, is a potential substance 4. -Wed carbohydrate man. 5. Different in the gastrointestinal tract 60. Select carbohydrate derivatives included in the Mural:

1.N-acetylglucosamine 2.N-acetylmoramic acid 3. Glucosamine 4. Glucuroic acid 5.Ribulose-5-phosphate 61.Select from the following statements correct: amino acids are ...

1. Compounds containing in the molecule at the same time amino and hydroxy group 2. Compounds containing hydroxyl and carboxyl groups 3. The carboxylic acid derivatives in the radical of which hydrogen is substituted on the amino group 4. Compounds containing in the oxo molecule and carboxyl group 5. Connections containing Oxy and aldehyde groups 62. How class classified amino acids?

1. By the chemical nature of the radical.

1. Glycine 2. Serine 3. Glutamine 4.Phenylalanine 5.Metionine 64.Select the amino acid exhibiting acid properties:

1.Lescin 2.Tripotofan 3. Glycine 4.Hlutamin 5.Line 65.Select the primary amino acid:

1. Serine 2.Lizin 3.Alin 4.Hlutamin 5.Triptopan 66.Select purine nitrogenous bases:

1.Timin 2.Adenin 3.Guananine 4.Surezil 5.Sitozin 67. Select pyrimidine nitrogen bases:

1.URAURCIL 2.Timin 3.Sitozin 4.Adenin 5.Guanin 68.Select the components of the nucleoside:

1.Purine nitrogen bases 2.Pyrimidine nitrogenous bases 3. Releases 4. Sexicity 5. Phosphoric acid 69. Here the structural components of nucleotides:

1.Purine nitrous bases 2. Pyrimidine nitrogenous bases 3. POBUS 4. Sexicity 5. Phosphoric acid 70.Dell a distinguishing feature of DNA:

1. Found by one polynucleotide chain 2. Educated by two polynucleotide chains 3. Conducts ribosa 4. Low deoxyribose 5. Suitable Uracil 6. Suitable Timin 71.Select the washesy lipids:

1.Nextral fats 2.TRiacyl glycerolines 3.Pospholipids 4.sFingomines Sinteroids 72. Select unsaturated fatty acids:

1.Palmitis 2.Shearine 3. olenovaya 4.INOLOLE 5.Arachidone 73.Tell, the characteristic composition of neutral fats:

1.Mericyl alcohol + palmitic acid 2. Glycerin + oil acid 3.Sfingosine + phosphoric acid 4. Glycerin + highest carboxylic acid + phosphoric acid 5. Glycerin + higher carboxylic acids 74.Select what function phospholipids in the human body are performed:

1. Regulatory 2. Protective 3. Design 4. Energy 75.Select glycolipids:

1. Fosphatidylcholine 2. Cebrosida 3.Sfinomyelin 4.Sulfatide 5. Gangliosides

Answers to test tasks

8.4 List of practical skills and tasks (in full) required for delivery 1. The ability to classify organic compounds on the structure of the carbon skeleton and by 2. The ability to draw up formulas by names and call on the structural formula typical representatives of biologically important substances and medicines.

3. The ability to allocate functional groups, acidic and main centers, conjugate and aromatic fragments in molecules to determine chemical behavior 4. Ability to predict the direction and result of the chemical transformations of organic 5. possessing the skills of independent work with educational, scientific and reference literature; Search and make generalizing conclusions.

6. Having a chemical dishes handling skills.

7. Having the skills of safe work in the chemical laboratory and the ability to handle caustic, poisonous, volatile organic compounds, working with burners, alcohol and electric heating devices.

1. The subject and tasks of bioorganic chemistry. Meaning in medical education.

2. Elementary composition of organic compounds, as the cause of their compliance with biological processes.

3. Classification of organic compounds. Classes, general formulas, funkonal groups, individual representatives.

4. Nomenclature of organic compounds. Trivial names. Replacement nomenclature of the Jew.

5. The main functional groups. Rhodonachable structure. Deputy. Seniority of groups, deputies. Names of functional groups and substituents as a prefix and end.

6. Theoretical foundations of the structure of organic compounds. Theory A.M. Butlerova.

Structural formulas. Structural isomeria. Isomers chains and positions.

7. Spatial structure of organic compounds. Stereochemical formulas.

Molecular models. The most important concepts in stereo-configurations and conformation of organic molecules.

8. Conformations of open chains - obscured, inhibited, beveled. Energy and reactivity of various conformations.

9. Conformations of cycles on the example of cyclohexane (chair and bath). Axial and equatorial connections.

10. The influence of atoms in organic compound molecules. His reasons, types of manifestation. Effect on the reaction capacity of molecules.

11. Conditions. Conjugated systems, conjugate connections. Pyi pairing in dienes. Energy of pairing. Stability of conjugate systems (vitamin A).

12. Conditions in the Arena (PI-PI Course). Aromaticity. Hyukkel rule. Benzole, Naphthalene, Fenantrene. The reactivity of the benzene ring.

13. Conditions in heterocycles (p-pp and pi-pi pairing on the example of pyrrole and pyridine).

The stability of heterocycles is biological significance on the example of tetrapyrrol compounds.

14. Reolarization of connections. The reasons. Polarization in alcohols, phenols, carbonyl compounds, thiola. Effect on the reaction capacity of molecules. \\ 15.Electronic effects. Inductive effect in molecules containing, sigma-links. Inductive effect sign.

16.Merry effect in open circuits with conjugate PI bonds on the example of butadiene-1,3.

17.Merry effect in aromatic compounds.

18.Electronic and electron substituents.

19. Officers of the I-go and II. Rule of orientation in the benzene ring.

20.Citness and basicity of organic compounds. Acids and bases of Brandstay Lowry.

Acid-major pairs are conjugated acids and again. KA and PKA - quantitative characteristics of the acidity of organic compounds. The value of acidity for the functional activity of organic molecules.

21.Citness of various classes of organic compounds. The factors that determine the acidity of organic compounds are the electronegability of the non-metallium atom associated with hydrogen, the polarizability of the non-metal atom, the nature of the radical associated with the nonmetal atom.

22.ganic grounds. Amines. Cause of basicity. The effect of radical on the basicity of aliphatic and aromatic amines.

23. Classification of the reactions of organic compounds by their mechanism. The concepts of homolitic and heterolitic reactions.

24. Recovery on the radical type of alkanes. Free-radical oxidation in living organisms. Active forms of oxygen.

25.Electrophilic attachment in alkenes. The formation of PI complexes, carboations. Hydration reactions, hydrogenation.

26.Electrophilic replacement in the aromatic core. The formation of intermediate sigmacomplexes. Benzol bromination reaction.

27.Nextoophilic replacement of alcohols. Dehydration reactions, oxidation of primary and secondary alcohols, ethers formation.

28.Nextoophilic connection in carbonyl compounds. Biologically important aldehyde reactions: oxidation, the formation of semi-acetals when interacting with alcohols.

29.Notoophilic replacement in carboxylic acids. Biologically important carboxylic acid reactions.

30.Oc acidification of organic compounds, biological significance. The degree of carbon oxidation in organic molecules. Oxidation of different classes of organic compounds.

31. Energy oxidation. Oxidase reactions.

32.Nenergetic oxidation. Oxygenase reactions.

33.Rol free-radical oxidation in the bactericidal action of phagocytic cells.

34. Restoration of organic compounds. Biological significance.

35. Polyifunctional compounds. Multiatomic alcohols - ethylene glycol, glycerin, xylitis, sorbitol, inosit. Biological significance. Biologists are important glycerol reactions - oxidation, formation of esters.

36. Double dicarboxylic acids: oxal, malonic, amber, glutar.

Transformation of succinic acid into fumarois - an example of biological dehydrogenation.

37.amines. Classification:

By the nature of the radical (aliphatic and aromatic); - by the amount of radicals (primary, secondary, tertiary, quaternary ammonium bases); - by the amount of amino groups (mono- and diamine-). Diamine: Pretssin and Cadaver.

38.Getherofunctional compounds. Definition. Examples. Features of manifestation of chemical properties.

39.Nicompirts: ethanolamine, choline, acetylcholine. Biological significance.

40. Oxycycles. Definition. General formula. Classification. Nomenclature. Isomeria.

Representatives of monocarbonic oxycoslot: dairy, beta-hydroxymalas, gamma-xymasalya;

dicarboxyls: Apple, Wine; tricarboxyls: lemon; Aromatic: Salicyl.

41. Chemical properties of oxic acid: for carboxyl, by a suites group, dehydration reaction in alpha, beta and gamma-isomers, distinction of reaction products (lactides, unsaturated acids, lactones).

42.Steroisomeria. Enantiomers and diastereomers. The chirality of organic compound molecules as the cause of the optical isomerism.

43.Nantiomers with one center of chirality (lactic acid). Absolute and relative configuration of enantiomers. Oxyxic acid key. D and L glycerin aldehyde. D and L isomers.

Racemates.

44.Nantiomers with several chirality centers. Wine and meson acids.

45.Steroisomeria and biological activity of stereoisomers.

46. \u200b\u200bCentral and trans isomeria on the example of fumarone and maleic acids.

47.Oxiscovers. Definition. Biologically important representatives: peer-grade, acetoxus, oxhelevoacetic. Ketoenol tautomeria on the example of pyruogradic acid.

48.Amino acids. Definition. General formula. Isomers of the position of amino group (alpha-, beta, gamma-). The biological value of alphaaminoxot. Representatives of beta, gamma, and other isomers (betaminopropionic, gammaamic-oil, epsilonamicapron). The reaction of the dehydration of gamma-isomers with the formation of cyclic lactones.

49.Getherofunctional derivatives of benzene, as the basis of medicines. Derivatives of P-aminobenzoic acid - PABK (folic acid, anesthesine). PABK antagonists derivatives of sulfanyl acid (sulfonamides - streptocid).

50.Getherofunctional derivatives of benzene - drugs. Raminofenol derivatives (paracetamol), salicylic acid derivatives (acetylsalicylic acid). Raminosalcyl Acid - Pask.

51.Biologically important heterocycles. Definition. Classification. Features of the structure and properties: conjugation, aromatic, stability, reactivity. Biological significance.

52.Thisted heterocycles with one heteroatom and their derivatives. Pyrrol (Porphine, Porphyrins, Gem), Furan (drugs), thiophene (biotin).

53.The heterocycles with two heteroatoms and their derivatives. Pirazole (5-power produced), imidazole (histidine), thiazole (vitamin B1-thiamine).

54.Stended heterocycles with one heteroatom and their derivatives. Pyridine (Nicotinic Acid is participation in oxidative reaction reactions, vitamin B6-pyridoxal), quinoline (5-nct), isoquinoline (alkalloids).

55.tened heterocycles with two heteroatoms. Pyrimidine (cytosin, Uracil, Timin).

56.Conned heterocycles. Purin (Adenin, Guanin). Pyrine oxidation products hypoxanthine, xanthin, urinary acid).

57.Talloids. Definition and general characteristics. The structure of nicotine and caffeine.

58.Glip. Definition. Classification. Functions of carbohydrates in living organisms.

59.monoshara. Definition. Classification. Representatives.

60.Tentoses. Representatives - robosis of the deoxyribosis. Building, open and cyclic formulas. Biological significance.

61.Gexose. Aldoz and ketosis. Representatives.

62. Open formulas of monosachar. Definition of stereochemical configuration. Biological configuration of monosachar.

63. Education of cyclic forms of monosacharov. Glycosidoid hydroxyl. Alpha and Betanetomiers. The formulas of Heuors.

64.Production of monosacharov. Phosphoric esters, glyacon and glycuronic acids, aminosahara and their acetyl derivatives.

65. Maltosis. Composition, structure, hydrolysis and value.

66.Lactose. Synonym. Composition, structure, hydrolysis and value.

67.Asaches. Synonyms. Composition, structure, hydrolysis and value.

68.Gomopolisaccharides. Representatives. Starch, structure, properties, hydrolysis products, value.

69.glyogen. Building, role in an animal body.

70.Fillet. Building, role in plants, value for humans.

72.Getheropolisaccharides. Synonyms. Functions. Representatives. Feature structure-dimeric links, composition. 1,3- and 1,4-glycoside ties.

73.galuronic acid. Composition, structure, properties, value in the body.

74. Chondroitin Sulfate. Composition, structure, value in the body.

75.Muramin. Composition, value.

76. Falia amino acids. Definition. General formula. Nomenclature. Classification. Separate representatives. Stereoisomeria.

77.Chemical properties of alphaaminoxot. Amphoteriness, decarboxylation, deamination reaction, hydroxylation in the radical, the formation of peptide communication.

78.Peptides. Individual peptides. Biological role.

79.Lork. Protein functions. Structure levels.

80.Azotic bases of nucleic acids - purines and pyrimidines. Modified nitrogen bases - antimetabolites (fluoruracyl, mercaptopurine).

81.Noteosides. Nucleosides antibiotics. Nucleotides. Mononucleotides in the composition of nucleic acids and free nucleotides - coherents.

82.Nokleinic acids. DNA and RNA. Biological significance. The formation of phosphodieter ties between mononucleotides. Levels of the structure of nucleic acids.

83.Lipids. Definition. Biological role. Classification.

84. High carboxylic acids - saturated (palmitic, stearin) and unsaturated (olein, linoleic, linolen and arachidon).

85.Nextral fats - acylglycerin. Building, value. Animals and vegetable fats.

Hydrolysis of fats - products, meaning. Hydrogenation of vegetable oils, artificial fats.

86. Glycerofospholipids. Building: phosphatide acid and nitrogenous bases.

Phosphatidylcholine.

87.Sfingolipids. Structure. Sphinosin. Sfigomyelin.

88.Steroids. Cholesterol - structure, value, derivatives: bile acids and steroid hormones.

89.Things and terpenoids. Building and biological significance. Representatives.

90. Healthy vitamins. General characteristics.

91. Means for anesthesia. Diethyl ether. Chloroform. Value.

92. Medicines for metabolic processes stimulants.

93. Sulfonamides, structure, meaning. White streptocid.

94. Antibiotics.

95. Anti-inflammatory and antipyretic means. Parasetamol. Structure. Value.

96. Antioxidants. Characteristic. Value.

96. Tiol. Antidotes.

97. Anticoagulants. Characteristic. Value.

98. Barbiturates. Characteristic.

99. Analgesics. H. Examples. Acetylsalicylic acid (aspirin).

100. Antiseptics. Value. Examples. Fucylin. Characteristic. Value.

101. Antiviral drugs.

102. Digestons.

103. Means for parenteral nutrition.

104. PABK, PASK. Structure. Characteristic. Value.

105. iodoform. Xeroform.

106. Polyglyukin. Characteristic. Value 107.Formal. Characteristic. Value.

108. Xylitis, sorbitol. Building, value.

109. Resorcin. Building, value.

110. Atropine. Value.

111. Caffeine. Structure. Meaning 113. Furacilin. Furazolidon. Characteristic. Description.

114. GABA, GOM, AMERIC Acid .. Building. Value.

115. Nicotinic acid. Building, value

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The subject of bioorganic chemistry.
The structure and isomerism of organic
connections.
Chemical bond and mutual influence
Atoms in organic compounds.
Types chemical reactions.
Poly and heterofunctional
Connections.
The main textbook - Tubavkina N.A., Baukov Yu.I.
Bioorganic chemistry.
Text of lectures and benefits "Bioorganic chemistry in
Questions and answers "See on TSU website http://tgumed.ru
Tab "Student Help", section "Lectures on
curriculum disciplines. " And, of course, VK

Bioorganic chemistry studies the structure and properties of substances involved in the processes of life, in connection with the knowledge of their biological

Bioorganic chemistry studies the structure and properties of substances,
participating in the processes of life, in connection with
knowledge of their biological functions.
Biological objects of study are the main objects
Polymers (biopolymers) and bioregulators.
Biopolymers
–
High molecular weight
Natural
compounds that are the structural basis of all living
organisms and playing a role in processes
vital activity. Biopolymers include peptides and
Proteins, polysaccharides (carbohydrates), nucleic acids. IN
This group includes lipids that themselves are not
are high molecular weight connections, but in
The body is usually associated with other biopolymers.
Bioregulators - connections that are chemically
Regulate the metabolism. These include vitamins,
Hormones, many synthetic biologically active
Compounds, including medicinal substances.

The combination of chemical reactions occurring in the body is called metabolism, or metabolism. Substances formed in cells, TK

A combination of chemical reactions occurring in the body,
Call metabolism, or metabolism. Substances
formed in cells, tissues and organs of plants and animals
In the process of metabolism, called metabolites.
Metabolism includes two directions - catabolism and
anabolism.
Catabolism refers to the decay reaction of substances falling
in the body with food. As a rule, they are accompanied by oxidation of organic compounds and proceed with highlighting
Energy.
Anabolism is the synthesis of complex molecules from
More simple, as a result of which the formation and update of the structural elements of the living organism is carried out.
Metabolic processes proceed with the participation of enzymes,
those. Specific proteins that are in cells
organism and play the role of catalysts biochemical
processes (biocatalysts).

Metabolism

catabolism
anabolism
Disintegration of biopolymer
With excretion
Energy
Synthesis of biopolymer
With absorption
Energy
Glycerin I.
fatty acid

The main provisions of the structure of the structure of organic compounds A.M. Butlerova

1. Atoms in the molecule are located in a certain
Sequences according to their valence.
Valence of carbon atom in organic
connections are four.
2. The properties of substances depend not only on what
Atoms and in what quantities are part of
molecules, but also on what order they are
Interconnected.
3. Atoms or groups of atoms that are part of
molecules, mutually affect each other, from what
dependence of chemical activity and reaction
The ability of molecules.
4. The study of the properties of substances allows you to define them
Chemical structure.

G about m about l about g and ch e s to and y r

Homological
row
A number of similarities in the structure of compounds possessing
close chemical properties in which individual
members of a series differ from each other only
groups -CH2-, called homologous near, and a group
CH2 - homologous difference.
Members of any homologous series overwhelming
Most reactions proceed equally (exception
Only the first members of the series are constituted). Consequently, knowing
Chemical reactions of only one member of the series can be with
a great degree of likelihood to say that the same
Type of transformation proceed with other members
Homological series.
For any homologous series can be removed
General formula reflecting the ratio between atoms
carbon and hydrogen in members of this series; Such formula
called the general formula of the homologous series.

Classification of organic compounds on the structure of the carbon skeleton

Classification of organic compounds for the availability of functional groups

Functional group
Class
Example
Halogens atoms (F, Cl, Br, I) halogen derivatives of CH3SN2CL (chloroethane)
hydroxyl (-on)
Alcohols (phenols)
CH3SN2ON (ethanol)
Tiolny or Mercpto- (- Tiol (Mercaptan) CH3SN2SN (etanalty)
SN)
Essential (-)
Simple ethers
CH3SN2-O-CH2SH33
(Diethyl
ether)
Complete ester
Carboxyl -s-° C.
Essentials
CH3SN2CO33 (methyl acetate)
Carboxylic acids CH3Cone (acetic acid)
Amid-off ONN2.
amides
carbonyl (-s \u003d o)
Sulfo- (-SO3N)
Amino- (-NH2)
Aldehydes I.
ketones
Sulfocislot
Amines
nitro- (-nO2)
Nitro compound
Acid
CH3CONN2 (acetamide)
CH3CO (ethanal)
CH3SN3 (propanone)
CH3SO3N (methanesulfonic acid)
CH3SN2NH2.
(ethylamine,
Primary amine)
CH3NHS3.
(dimethylamine,
Secondary Amin)
CH3SN2NO2 (nitroean)

Nomenclature of organic compounds

Isomerius of organic compounds

If two or more individual substances have
the same quantitative composition (molecular formula),
But differ from each other sequence of binding
atoms and (or) arrangement in space, then in general
The case they are called isomers.
Since the structure of these compounds is different, then
Chemical or physical properties of isomers
differ.
Types of isomerism: structural (isomers of the structure) and
Stereoisomeria (spatial).
Structural isomeria can be three species:
- isomerism of the carbon skeleton (chain isomers),
- Isomers of the situation (multiple connections or functional
groups)
- Isomers of the functional group (interclass).
Stereoisomeria is divided
configuration
on the
conformational
and

Here is such a geometric isomeria

Flat-polarized light

Signs of optical activity:
- the presence of an asymmetric carbon atom;
- no molecule symmetry elements

Adrenaline enantiomers
protein
Anionic
Flat
Centre
surface
not occupied
Flat
Anionic
surface
Centre
Busy
(+) - adrenaline
(-) - adrenaline
incomplete
conformity
Low
activity
Full
conformity
High
activity

Biological activity of enantiomers

asparagin
Darwon
analgesic
Novura
Anti-tech drug
mirror
L-Asparagin
D-Asparagin
(from asparagus)
(from peas)
bitter taste
Sweet taste
Enantiomers
Victims of Talidomid

Acidness and basicity of organic compounds

Brensman acids (proton acids) -
Neutral molecules or ions capable
Give proton (protons donors).
Typical acids according to Brenster - Carbon
Acids. More weak acid properties have
hydroxyl groups of phenols and alcohols, as well as thi-,
amino and intriguing.
The bases of Brensted - neutral molecules or
Ions capable of attaching Proton (acceptors
Protons).
Typical bases on Brenets - amines.
Ampholites - compounds in molecules
which are also acidic and
Basic groups.

Types of acids and bases by Broncester

Major centers in Novocaina Molecule

Use of basic properties to obtain water-soluble forms of drugs

Maintenance
Properties
medicinal
drugs
Used to obtain their water soluble forms.
When interacting with acids, connections are formed with
Ionic bonds - salts, well-soluble in water.
So, Novocain for injection
It is used in the form of hydrochloride.
The most powerful main center,
to which the proton joined

Acid and basic properties of substances and their entry into the body

lipid
membrane
PH stomach 1.
Soon
Lipid
membrane
Plasma blood
pH 7,4.
Soon
Ososn3
PH stomach 1.
+
Ososn3
NH3
SOOSN3.
Co-
NH2.
NH2.
Ososn3
Intestinal pH 7-8
Plasma blood
pH 7,4.
Intestinal pH 7-8
Acid nature preparations are better absorbed from the stomach (pH 1-3),
and suction of drugs or xenobiotics based only
Once they go out of the stomach in the intestine (pH 7-8). During
One hour from the stomach rats is absorbed by almost 60% acetylsalicyl
Acids and only 6% aniline from the administered dose. In the intestines of rats
It is already absorbed by 56% of the introduced dose of aniline. Such a weak basis
as caffeine (RKVH + 0.8), absorbed during the same time in much greater
degrees (36%), because even in the strongly acidic medium of the stomach caffeine
mainly in the non-ionized state.

Types of reactions in organic chemistry

Organic reactions are classified by
The following features:
1. by electronic reagents.
2. By changing the number of particles during the reaction.
3. On private features.
4. In the mechanisms of elementary
Stages of reactions.

Depending on the electronic nature of the reagents, reactions are distinguished: nucleophilic, electrophilic and free radical

Free radicals are electronic particle particles,
Having an unpaired electron, for example: Cl, NO2.
Free radical reactions are characteristic of alkanans.
Electropil reagents are cations or molecules,
which themselves or in the presence of a catalyst
possess increased affinity for electronic pair or
Negatively charged centers of molecules. These include
Cations H +, CL +, + NO2, + SO3H, R + and molecules with free
Alcl3 orbitals, ZnCl2, etc.
Electrophilic reactions are characteristic of alkenes, alkins,
aromatic compounds (double-bond attachment,
Proton replacement).
Nucleophilic reagents are an anions or molecules,
Having centers with increased electron density. To them
include such anions and molecules as
HO-, RO-, CL-, BR-, RCOO-, CN-, R-, NH3, C2H5OH, etc.

By change
Particle numbers during
Reactions are distinguished
Reaction reactions,
joining
Spliced
(elimination),
decomposition

Classification of reactions by private features

Reactivity is always considered
Only in relation to the reaction partner.
During the chemical transformation usually
not the whole molecule is affected, but only its part -
Reaction Center.
In the organic connection may be present
Several unequal reaction centers.
Reactions can lead to isomeric products.
Reaction selectivity - high-quality
Characteristic meaning preferential
The flow of reaction in one direction from
Several possible.
Distinguish regional
Hemoselectivity, reaction stereo selectivity.

Selectivity of reactions in organic chemistry

Region selectivity - preferred response
One of several reaction centers of the molecule.
CH3-CH2-CH3 + BR2
CH3-STAR-CH3 + HBR
The second isomer, 1-bromopropane, is practically not formed.
Chemoselectivity - Preferred reaction flow
One of the related functional groups.
Stereo selectivity - preferred education in the reaction
One of several possible stereoisomers.

Polyfunctional compounds contain
Several identical functional groups.
Heterofunctional compounds contain
Several different functional groups.
Heteropolifunctional
Compounds contain as
various and the same
Functional groups.

Properties of poly and heterofunctional compounds

Each group in poly and heterofunctional
compounds can enter into the same reactions as
The corresponding group in monofunctional
Connections

Specific properties of poly- and
heteroofunctional compounds
Cyclization reactions
The formation of chelate complexes

Polyfunctional compounds like antidote
The toxic effect of heavy metals is
binding of quiol groups of proteins. As a result, inhibit
Vital enzymes of the body.
The principle of action of antidotot - the formation of durable
Complexes with heavy metal ions.

Bioorganic chemistry. Tubavkina N.A., Baukov Yu.I.

3rd ed., Pererab. and add. - M.: 2004 - 544 p.

The main feature of the textbook is a combination of the medical orientation of this chemical course required for medical students with its high, fundamental scientific levels. The textbook includes a base material on the structure and reactivity of organic compounds, including biopolymers that are the structural components of the cell, as well as basic metabolites and low molecular weight bioregulators. In the third edition (2nd - 1991), special attention was paid to compounds and reactions with analogies in a living organism, emphasized emphasis on the coverage of the biological role of important compound classes, expanded the spectrum of modern information of ecological and toxicological nature. For students of universities, studying by the specialties of 040100 therapeutic case, 040200 Pediatrics, 040300 Medical and prophylactic case, 040400 Dentistry.

Format: PDF.

The size: 15 MB

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CONTENT
Preface ...................... 7.
Introduction ......................... 9.
Part I.
Basics of structure and reactivity of organic compounds
Chapter 1. General characteristics of organic compounds 16
1.1. Classification. "................ sixteen
1.2. . Namenclature ... ............ 20
1.2.1. Replacement nomenclature ........... 23
1.2.2. Radical and functional nomenclature ........ 28
Chapter 2. Chemical bond and mutual influence of atoms in organic
Connections .................. 29.
2.1. Electronic structure of organogen elements ...... 29
2.1.1. Atomic orbitals ................ 29
2.1.2. Hybridization of orbitals ............. 30
2.2. Covalent bonds ............... 33
2.2.1. A- and L-bonds .................. 34
2.2.2. Donor-acceptor connections ............ 38
2.2.3. Hydrogen bonds ............... 39
2.3. Conjugation and aromatics ............ 40
2.3.1. Interface open circuit systems ..., ..... 41
2.3.2. Systems with a closed pairing chain ........ 45
2.3.3. Electronic effects .............. 49
Chapter 3. Basics of the structure of organic compounds ....... 51
3.1. Chemical structure and structural isomeria ...... 52
3.2. Spatial structure and stereoisomeria ...... 54
3.2.1. Configuration ................. 55.
3.2.2. Conformation ................. 57.
3.2.3. Elements of symmetry of molecules ............ 68
3.2.4. EIInhythomeria ............... 72.
3.2.5. Diastereomeria ................
3.2.6. Racemates .................. 80.
3.3. Enantiotopia, diastereotopy. . ......... 82.
Chapter 4 General Characteristics of Organic Compound Reactions 88
4.1. The concept of the reaction mechanism ..... 88
3
11.2. Primary structure of peptides and proteins ........ 344
11.2.1. Composition and amino acid sequence ...... 345
11.2.2. The structure and synthesis of peptides ............ 351
11.3. Spatial structure of polypeptides and proteins .... 361
Chapter 12. Carbohydrates .................... 377
12.1. Monosaccharides ................. 378.
12.1.1. Building and stereoisomeria ............. 378
12.1.2. Tautomeria ................ 388
12.1.3. Conformations ................. 389.
12.1.4. Monosaccharide derivatives ............ 391
12.1.5. Chemical properties ............... 395
12.2. Disaccharides .................. 407.
12.3. Polysaccharides ................. 413
12.3.1. Homopolisaccharides ............... 414.
12.3.2. Heteropolysaccharides ............... 420.
Chapter 13. Nucleotides and nucleic acids .......... 431
13.1. Nucleosides and nucleotides ............. 431
13.2. The structure of nucleic acids ........... 441
13.3 nucleosidepolyphosphates. Nicotinemindnucleotides ..... 448.
Chapter 14. Lipids and low molecular weight bioregulators ...... 457
14.1. Washed lipids ............... 458
14.1.1. Higher fatty acids - structural components of washythic lipids 458
14.1.2. Simple lipids ................ 461
14.1.3. Complex lipids ................ 462
14.1.4. Some properties of washylable lipids and their structural components 467
14.2. Unlimited lipids 472.
14.2.1. Terpered .......... ...... 473
14.2.2. Low molecular weight bioregulators lipid Nature. . . 477
14.2.3. Steroids ................... 483.
14.2.4. The biosynthesis of terpenes and steroids ........... 492
Chapter 15. Methods of research of organic compounds ...... 495
15.1. Chromatography ................. 496
15.2. Analysis of organic compounds. . ........ 500
15.3. Spectral methods ............... 501
15.3.1. Electronic spectroscopy ............. 501
15.3.2. Infrared spectroscopy ............ 504
15.3.3. Nuclear magnetic resonance spectroscopy ...... 506
15.3.4. Electronic paramagnetic resonance......... 509
15.3.5. Mass spectrometry ............... 510

Preface
Through the centuries-old history of the development of natural science, a close relationship between medical and chemistry was established. Currently, the deep interpenetration of these sciences leads to the emergence of new scientific directions studying the molecular nature of individual physiological processes, the molecular foundations of pathogenesis of diseases, molecular aspects of pharmacology, etc. The need for knowledge of life processes at the molecular level is explained, "For a live cell - the present The kingdom of large and small molecules, continuously interacting, emerging and disappearing "*.
Bioorganic chemistry studies biologically significant substances and can serve as a "molecular instrument" with a versatile study of cell components.
Bioorganic chemistry plays an important role in the development of modern medicine areas and is an integral part of a physician natural science education.
The progress of medical science and health improvement are related to the deep fundamental training of specialists. The relevance of this approach is largely determined by the transformation of medicine into a large branch of the social sphere, in the field of view of which there are problems of ecology, toxicology, biotechnology, etc.
Due to the lack of medical universities of the general course of organic chemistry, the general course of organic chemistry in this textbook is given a certain place of the basics of organic chemistry necessary for the assimilation of bioorganic chemistry. In preparing the third edition (2nd - 1992), the material of the textbook was redesigned and even more close to the tasks of the perception of medical knowledge. Expanded the circle of compounds and reactions with analogies in living organisms. More attention is paid to the information of an environmental and toxicological nature. Elements of a purely chemical nature have been subjected to some reduction, which have no fundamental importance for medical educationIn particular, methods for obtaining organic compounds, properties of a number of individual representatives, etc. At the same time, sections are expanded comprising material about the relationship between the structure of organic substances and their biological effect as a molecular basis of the action of drugs. The textbook structure has been improved, a chemical material has a special biomedic value into separate headings.
The authors express our sincere thanks to Professors S. E. Zrabyan, I. Yu Belavin, I. A. Selivanova, as well as all colleagues for useful tips and assistance in preparing a manuscript to reprint.

Chemistry- science on the structure, properties of substances, their transformations and accompanying phenomena.

Tasks:

1. Study of the structure of the substance, the development of the theory of the structure and properties of molecules and materials. It is important to establish a connection between the structure and various properties of substances and on this basis the construction of the theories of the reaction capacity of the substance, kinetics and the mechanism of chemical reactions and catalytic phenomena.

2. Implementation of the directional synthesis of new substances with specified properties. It is also important to find new reactions and catalysts for more effective implementation of the synthesis of already known and having industrial import value.

3. The traditional task of chemistry has gained special importance. It is associated both with an increase in the number of chemical objects and studied properties and the need to determine and reduce the effects of human impact on nature.

Chemistry is generalory discipline. It is designed to give students a modern scientific view of a substance as one of the types of moving matter, about the paths, mechanisms and methods of transforming one substances into others. Knowledge of basic chemical laws, ownership of chemical calculation techniques, an understanding of the possibilities provided by chemistry with the help of other specialists working in individual and narrow areas, significantly accelerates obtaining the necessary result in various areas of engineering and scientific activities.

The chemical industry is one of the most important industries in our country. Produced by her chemical compounds, various compositions and materials are used everywhere: in mechanical engineering, metallurgy, agriculture, construction, electrical and electronic industry, communications, transport, space technology, medicine, everyday life, etc. The main directions of development of the modern chemical industry are: the production of new compounds and materials and improving the efficiency of existing industries.

In a medical university, students explore common, bioorganic, biological chemistry, as well as clinical biochemistry. Knowledge by students of the complex of Chemical Sciences in their continuity and relationships give a greater opportunity, greater space in the study and practical use of various phenomena, properties and patterns, contributes to the development of the personality.

Specific features of studying chemical disciplines in medical university are:

· Interdependence between chemical and medical education purposes;

· Universality and fundamentality of these courses;

· Feature of building their content, depending on the nature and general objectives of the training of a doctor and its specialization;

· Unity of studying chemical objects on micro- and macro levels with the disclosure of different forms of their chemical organization as a single system and manifest themselves different functions (chemical, biological, biochemical, physiological, etc.), depending on their nature, environment and conditions;

· Dependence on the connection of chemical knowledge and skills with real reality and practice, including medical, in the Society - Nature - Manufacturing - Manufacturing system, due to the unlimited possibilities of chemistry in the creation of synthetic materials and their meaning in medicine, the development of nanochemistry, as well as In solving the environmental and many other global problems of humanity.

1. The relationship between the process of metabolism and energy in the body

The processes of life on Earth are due to a large extent with the accumulation of solar energy in biogenic substances - proteins, fats, carbohydrates and subsequent transformations of these substances in living organisms with energy release. Especially clearly understanding the relationship of chemical transformations and energy processes in the body was conscious after works A. Lavoisier (1743-1794) and P. Laplas (1749-1827). They show direct calorimetric measurements that the energy that is secreted in the process of life is determined by the oxidation of the food of the air, inhaled animals.

The exchange of substances and energy is a set of processes of transformation of substances and energy occurring in living organisms and the exchange of substances and energy between the organism and the environment. The metabolism and energy is the basis of the vital activity of organisms and belongs to the number of most important specific signs of living matter, distinguishing living from non-living. In the exchange of substances, or metabolism provided by the most complex regulation at different levels, many enzyme systems are involved. In the process of exchange, the substances received in the body are converted into eigenous substances of the tissues and to the final products that are separated from the body. With these transformations, energy is released and absorbed.

With development in the XIX-XX centuries. Thermodynamics - sciences of mutual and energies and energies - it became possible to quantify the conversion of energy in biochemical reactions and predict their direction.

Energy exchange can be carried out by heat transfer or performance. However, living organisms are not in equilibrium with the environment and therefore may be called non-equilibrium open systems. However, when observed over a certain period of time, there is no visible changes in the chemical composition of the organism. But this does not mean that the chemicals constituting the body are not subjected to any transformations. On the contrary, they are constantly and enough intensively updated, as can be judged by the speed of inclusion in complex substances stable isotopes and radionuclides introduced into a cell in the composition of simpler predecessor substances.

There is one between the exchange of substances and energy exchange fundamental difference. The land does not lose and does not receive any noticeable amount of substance. The substance in the biosphere exchanges on a closed cycle and that Used repeatedly. Energy exchange is carried out otherwise. It does not circulate along a closed cycle, but partly dissipated into the external space. Therefore, to maintain life on Earth, a constant inflow of the energy of the Sun is necessary. For 1 year in the process of photosynthesis on the globe absorbs about 10 21 cal.solar energy. Although it is only 0.02% of all the energy of the Sun, it is immeasurably greater than that energy that is used by all machines created by the hands of a person. As much as a large amount of substance participating in the circuit circuit.

2. Chemical thermodynamics as theoretical Foundation Bioenergy. The subject and methods of chemical thermodynamics

Chemical thermodynamicshe is studying the transitions of chemical energy into other forms - thermal, electrical, etc., sets the quantitative laws of these transitions, as well as the direction and limits of spontaneous flow of chemical reactions under specified conditions.

The thermodynamic method is based on a number of strict concepts: "System", "System Condition", "Internal Energy System", "System State Function".

Object learning in thermodynamics is the system

The same system can be in different states. Each system status is characterized by a specific set of thermodynamic parameters. The thermodynamic parameters include temperature, pressure, density, concentration, etc. The change of at least one thermodynamic parameter leads to a change in the state of the system as a whole. The thermodynamic state of the system is called equilibrium if it is characterized by the constancy of thermodynamic parameters in all points of the system and does not change spontaneously (without cost).

Chemical thermodynamics examines the system in two equilibrium states (finite and initial) and on this basis determines the possibility (or inability) of the spontaneous flow of the process under specified conditions in the specified direction.

Thermodynamics learnthe mutual transformations of various types of energy associated with the transition of energy between the bodies in the form of heat and work. Thermodynamics is based on two basic laws that have received the name of the first and second principle of thermodynamics. Subject of study In thermodynamics is the energy and laws of mutual transformations of energy forms in chemical reactions, dissolution processes, evaporation, crystallization.

Chemical thermodynamics - section of physical chemistry studying the processes of the interaction of substances by thermodynamic methods.
The main directions of chemical thermodynamics are:
Classical chemical thermodynamics studying thermodynamic equilibrium at all.
Thermochemistry learning thermal effectsaccompanying chemical reactions.
The theory of solutions modeling the thermodynamic properties of the substance based on the ideas about molecular structure and intermolecular interaction data.
Chemical thermodynamics closely comes into contact with such sections of chemistry as analytical chemistry; electrochemistry; colloid chemistry; Adsorption and chromatography.
The development of chemical thermodynamics was at the same time in two ways: thermochemical and thermodynamic.
The emergence of thermochemistry as independent science should be considered the discovery of Hermann Ivanovich Hesse, the professor of the St. Petersburg University, the relationship between the thermal effects of chemical reactions --- the laws of the hess.

3. Thermodynamic systems: isolated, closed, open, homogeneous, heterogeneous. The concept of phase.

System - This is a combination of interacting substances, mentally or virtually separate from the environment (test tube, autoclave).

Chemical thermodynamics considers transitions from one state to another, it may change or remain constant some parameters:

· isobaric - at constant pressure;

· isochoric - at a constant volume;

· isothermal - at a constant temperature;

· isobaro - isothermal - at constant pressure and temperature, etc.

Thermodynamic properties of the system can be expressed using several system status functions, called characteristic features: internal energy , entalpy H. , entropy S. , energy Gibbs G. , energy Helmholts F. . Characteristic functions have one feature: they do not depend on the method (path) of achieving this system status. Their value is determined by the parameters of the system (pressure, temperature, etc.) and depends on the amount or mass of the substance, so it is customary to belong to one praying of the substance.

According to the method of transmission of energy, substance and information between the system under consideration and the environment, thermodynamic systems are classified:

1. Closed (isolated) system - This is a system in which there is no exchange with external bodies either with energy or substance (including radiation) nor information.

2. Closed system - The system in which there is an exchange for only energy.

3. Adiabato isolated system -this is a system in which there is an exchange of energy only in the form of heat.

4. Open system - This is a system that is exchanged with energy, and substance and information.

System classification:
1) If possible, heat and mass transfer: isolated, closed, open. The isolated system does not exchange with the environment or substance nor energy. The closed system exchanges with the environment, but not exchanged substance. The open system exchanges with the environment and substance and energy. The concept of an isolated system is used in physical chemistry as a theoretical.
2) by internal structure and properties: homogeneous and heterogeneous. A homogeneous is called a system inside which there are no surfaces that divide the system on parts, various properties or chemical composition. Examples of homogeneous systems are aqueous solutions of acids, bases, salts; Gas mixtures; Individual pure substances. Heterogeneous systems contain inside natural surfaces. Examples of heterogeneous systems are systems consisting of various aggregate state Substances: metal and acid, gas and solid substance, two insoluble in each other liquid.
Phase - This is a homogeneous part of a heterogeneous system, having the same composition, physical and chemical properties separated from other parts of the system surface when switching through which the properties of the system are changing the jump. Phases are solid, liquid and gaseous. The homogeneous system always consists of one phase, heterogeneous - from several. According to the number of phases, the system is classified on single-phase, two-phase, three-phase, etc.

5. The first start of thermodynamics. Internal energy. Isobaric and isochhore thermal effects .

The first top of thermodynamics - One of the three major laws of thermodynamics is the law of conservation of energy for thermodynamic systems.

The first top of the thermodynamics was formulated in the middle of the XIX century as a result of the works of the German scientist Yu. R. Mayer, English physics J. P. Joule and German physics of Gelmholts.

According to the first beginning of the thermodynamics, the thermodynamic system can perform work only at the expense of its internal energy or any external sources of energy .

The first top of the thermodynamics is often formulated as the impossibility of the existence of the perpetual engine of the first kind, which would perform work, without drawing energy from a source. The process flowing at a constant temperature is called isothermal, at constant pressure - isobaric, at a constant volume - isohoric. If during the process the system is isolated from the external environment in such a way that heat exchange with the medium is excluded, the process is called adiabatic.

Internal energy system.When switching the system from one state to another, some of its properties change, in particular internal energy. U.

The internal energy of the system is its total energy, which consists of the kinetic and potential energies of molecules, atoms, atomic nuclei and electrons. Internal energy includes the energy of translational, rotational and oscillatory movements, as well as the potential energy due to the forces of attraction and repulsion acting between molecules, atoms and intra-mattar particles. It does not include the potential energy of the position of the system in the space and the kinetic energy of the system movement as a whole.

Internal energy is the thermodynamic function of the system status. This means that whenever the system turns out to be in this state, its internal energy takes a certain meaning of this state.

ΔU \u003d U 2 - U 1

where u 1 and u 2 - the internal energy of the system inthe finite and initial states are conspirable.

The first law of thermodynamics.If the system is exchanged with an external thermal energy of q and mechanical energy (work) A, and at the same time passes from state 1 in state 2, the amount of energy that is released or is absorbed by the heat forms of the heat or the work of the operation of the system in transition from one Status to another and recorded.

Bioorganic chemistry, studies the link between the structure of organic substances and their biological functions, using mainly methods of organic and physical chemistry, as well as physics and mathematics. Bioorganic chemistry fully covers the chemistry of natural compounds and partially intersects with biochemistry and molecular biology. The objects of its study are biologically important natural compounds - mainly biopolymers (proteins, nucleic acids, polysaccharides and mixed biopolymers) and low molecular weight biologically active substances - vitamins, hormones, antibiotics, toxins, and so on, as well as synthetic analogues of natural compounds, drugs, Pesticides, etc.

Bioorganic chemistry was formed as an independent area in the 2nd half of the 20th century at the junction of biochemistry and organic chemistry based on the traditional chemistry of natural compounds. Its becoming is associated with the names of L. Poling (the discovery of the α-helix and β-structure as the main elements of the spatial structure of the polypeptide chain in proteins), A. Todd (clarification of the chemical structure of nucleotides and the first synthesis of dinucleotide), F. Senger (Development of the Amino Acid Definition Mode sequences in proteins and decoding with its help of the primary insulin structure), V. du Vino (allocation, structure of structure and chemical synthesis of peptide hormones - oxytocin and vasopressin), D. Barton and V. Pravoga (conformational analysis), R. Woodvord (full chemical synthesis of many complex natural compounds, including reserpine, chlorophyll, vitamin B 12), etc.; In the USSR, the work of N. D. Zelinsky, A. N. Belozersky, I. N. Nazarova, N. A. Preobrazhensky, and others were played a huge role. Initiator of research on bioorganic chemistry in the USSR in the early 1960s was MM. Shemyakin. In particular, work was launched (subsequently received widespread development) on the study of cyclic depotides performing the function of ionophos. The leader of domestic bioorganic chemistry in the 1970-80s was Yu.A. Ovchinnikov, under the leadership of which the structure of dozens of proteins was established, including membrane (for the first time) - bacterioriopcin and visual Rhodopsin bull.

The main directions of bioorganic chemistry include:

1. Development of methods for isolating and cleaning natural compounds. At the same time, the specific biological function of the studied substance is often used to control the degree of purification (for example, the purity of the antibiotic is controlled by its antimicrobial activity, hormone - by its influence on a certain biological process, and so on). In the separation of complex natural mixtures, highly efficient liquid chromatography and electrophoresis are often used. Since the end of the 20th century, instead of searching and sewing individual components, a total screening of biological samples is carried out to the maximum possible number of components of a particular connection class (see proteomics).

2. Determination of the structure of studied substances. Under the structure, not only the establishment of nature and the order of communication of atoms in the molecule, but also their spatial location. For this purpose, various methods are used, primarily chemical (hydrolysis, oxidative splitting, treatment with specific reagents), allowing to obtain more simple substances With a known structure, which reconstruct the structure of the starting material. Automatic devices are widely used, providing a rapid solution of standard problems, especially in chemistry of proteins and nucleic acids: analyzers for the quantitative determination of amino acid and nucleotide composition and sequenters to determine the sequence of amino acid residues in proteins and nucleotides in nucleic acids. An important role in the study of the structure of biopolymers is played by enzymes, especially those that specifically cleave them according to strictly defined bonds (for example, proteinases, catalyzing peptide bonding reactions on glutamic acid residues, proline, arginine and lysine, or restrictions, specifically cleaving phosphodiester communications in polynucleotides ). Information on the structure of natural compounds is also obtained using physical research methods - mainly mass spectrometry, nuclear magnetic resonance and optical spectroscopy. Improving the efficiency of chemical and physical methods is achieved due to the simultaneous analysis of not only natural compounds, but also their derivatives containing characteristic, specially introduced groupings and labeled atoms (for example, by growing bacteria - producers of one or another compound on an environment containing precursors of this compound enriched stable or radioactive isotopes). The accuracy of the data obtained in the study of complex proteins is significantly increased by simultaneously studying the structure of the respective genes. The spatial structure of molecules and their analogues in the crystalline state is investigated by X-ray analysis. Resolution in some cases reaches values \u200b\u200bless than 0.1 nm. For solutions, the NMR method is most informative in combination with theoretical conformational analysis. Extension information is given optical spectral analysis methods (electronic and fluorescent spectra, spectra of circular dichroism, etc.).

3. Synthesis of both the natural compounds themselves and their analogues. In many cases, chemical or chemical-enzymatic synthesis is the only way to obtain the desired substance in large (preparative) quantities. For relatively simple low molecular weight compounds, the counter synthesis serves as an important criterion for the correctness of a previously defined structure. Automatic protein and polynucleotide synthesizers have been created, which can significantly reduce the synthesis time; With their help, a series of proteins and polynucleotides containing several hundred monomer units are synthesized. Chemical synthesis is a basic way to obtain non-drug drugs. In the case of natural substances, he often complements biosynthesis or competes with it.

4. Establishment of cell and molecular target, on which the effect of biologically is directed active substance, Finding out the chemical mechanism of its interaction with a living cell and its components. Understanding the molecular mechanism of action is necessary for productive use of biomolecules, with their often extremely high activity (for example, toxins), as instruments for researching biological systems; It serves as the basis for the directional synthesis of new, practically important substances with predetermined properties. In some cases (for example, when studying peptides affecting activities nervous system) The substances thus obtained have repeatedly reinforced, compared with the original natural prototype, modified in the right direction activity.

Bioorganic chemistry is closely related to the solution of practical problems of medicine and agriculture (obtaining vitamins, hormones, antibiotics and other medicines, plant growth stimulants, animal behavior regulators, including insects), chemical, food and microbiological industries. As a result of the combination of methods of bioorganic chemistry and genetic engineering, it became possible a practical solution to the problem of industrial production of complex, biologically important substances of protein-peptide nature, including such high molecular weight, as insulin of a person, α-, β- and γ-interferons, human growth hormone.

Lit.: Digid, Penny K. Bioorganic Chemistry. M., 1983; Ovchinnikov Yu. A. Bioorganic chemistry. M., 1996.