Биоорганическая химия (на английском языке) Биоорганическая химия (на английском языке) The textbook is based on modern organic chemistry and considers the structure and chemical transformations of organic compounds, especially those that have biological importance. Special attention is given to the chemical reactions that have analogies in living systems. The book contains about 250 problems on all topics and solutions for them. This book conforms to the Federal educational program on Bioorganic Chemistry for medical schools and universities. It is meant for students who study Bioorganic Chemistry during one term. The book may also be useful for teachers and students of specialized sec ondary schools with instruction conducted in English and colleges, whose main interest is medicine, pharmacy, biology and agriculture. ГЭОТАР-Медиа 5-9231-0474-1
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Биоорганическая химия (на английском языке)

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The textbook is based on modern organic chemistry and considers the structure and chemical
transformations of organic compounds, especially those that have biological importance. Special
attention is given to the chemical reactions that have analogies in living systems. The book contains
about 250 problems on all topics and solutions for them.
This book conforms to the Federal educational program on Bioorganic Chemistry for medical
schools and universities. It is meant for students who study Bioorganic Chemistry during one
term. The book may also be useful for teachers and students of specialized sec ondary schools with
instruction conducted in English and colleges, whose main interest is medicine, pharmacy, biology
and agriculture.
Отрывок из книги «Биоорганическая химия (на английском языке)»
Probably many students have already acquired some knowledge in a beginner’s
chemistry course. Nevertheless, it would be expedient to recall in this opening chapter
some information on general chemistry and the structural theory of organic chemistry
that will be helpful in studying the entire course.
1.1. THE STRUCTURAL THEORY OF ORGANIC COMPOUNDS
In the mid-nineteenth century (1858–1860), F.A. Kekul

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PREFACE

PART 1. GENERAL ASPECTS OF CHEMICAL STRUCTURE AND REACTIVITY OF ORGANIC COMPOUNDS

CHAPTER 1. CHEMICAL STRUCTURE AND BONDING

1.1. The Structural Theory of Organic Compounds

1.2. The Structure of Atoms

1.2.1. Atomic Orbitals

1.2.2. Electronic Configuration

1.3. The Nature of Chemical Bonding

1.3.1. Ionic Bonds

1.3.2. Covalent Bonds

1.4. Bonding in Carbon Compounds

1.4.1. sp3 Hybridization

1.4.2. sp2 Hybridization

1.4.3. sp Hybridization

1.4.4. Hybridization of Other Atoms

1.5. The Representation of Structural Formulas

1.6. Shape of Molecules and Molecular Models

Additional Problems

СHAPTER 2. CLASSIFICATION AND NOMENCLATURE OF ORGANIC COMPOUNDS

2.1. Classification

2.1.1. Classification According to the Molecular Framework

2.1.2. Classification According to Functional Groups

2.2. Nomenclature

2.2.1. General Principles of the IUPAC Nomenclature

2.2.2. General Principles of Forming a Systematic Name

2.2.3. Names of Parent Structures

2.2.4. Examples of Constructing the Systematic Names

Additional Problems

CHAPTER 3. ELECTRONIC STRUCTURE OF ORGANIC MOLECULES

3.1. Conjugation as Stabilizing Factor of Molecules

3.1.1. Conjugation

3.1.2. p. Conjugation

3.2. Aromaticity

3.2.1. Benzene

3.2.2. Modern Theories of the Structure of Benzene

3.3. Electronic Effects in Organic Molecules

3.3.1. Polar and Nonpolar Covalent Bonds

3.3.2. Inductive Effect

3.3.3. Mesomeric Effect

CHAPTER 4. A BRIEF SURVEY OF ORGANIC REACTIONS

4.1. Types of Organic Reactions

4.2. Reaction Mechanisms

4.2.1. Radical and Polar Processes

4.2.2. Types of Reagents

4.3. Energetics of Chemical Reactions

4.3.1. Activation Energy and Reaction Energy Diagram

4.3.2. Catalysis

Additional Problems

CHAPTER 5. ACIDITY AND BASICITY OF ORGANIC COMPOUNDS

5.1. General Concepts of Acids and Bases

5.2. Acids

5.2.1. Electronegativity and Polarizability of an Atom

5.2.2. Delocalization of a Charge in an Anion

5.2.3. Solvation Effects

5.3. Bases

5.4. Acidic and Basic Sites in a Molecule

Additional Problems

CHAPTER 6. HYDROCARBONS

6.1. Classification

6.2. Saturated Hydrocarbons

6.2.1. Conformational Isomerism

6.2.2. Chemical Properties

6.2.3. Cyclopropane

6.3. Unsaturated Aliphatic Hydrocarbons

6.3.1. Isomerism

6.3.2. Addition Reactions of Alkenes

6.3.3. Addition Reactions to Dienes

6.4. Aromatic Hydrocarbons

6.4.1. Electrophilic Aromatic Substitution

6.4.2. Substituent Effects in Electrophilic Aromatic Substitution

6.4.3. Oxidation and Reduction of Arenes

Additional Problems

PART 2. MONOFUNCTIONAL ORGANIC COMPOUNDS OF BIOLOGICAL INTERESTS

CHAPTER 7. ORGANIC HALIDES, ALCOHOLS, PHENOLS, ETHERS, AMINES, AND ORGANOSULFUR COMPOUNDS

7.1. Organic Halides

7.1.1. Nucleophilic Substitution Reactions

7.1.2. Elimination Reactions

7.2. Alcohols, Phenols, and Thiols

7.2.1. Classification and Nomenclature
7.2.2. Acidic and Basic Properties

7.2.3. Electrophilic and Nucleophilic Properties

7.2.4. Elimination Reactions

7.2.5. Oxidation Reactions

7.3. Ethers and Sulfides

7.4. Amines

7.4.1. Classification and Nomenclature

7.4.2. Chemical Properties

7.5. Biochemical Alkylations

Additional Problems

CHAPTER 8. CARBONYL COMPOUNDS

8.1. General Characteristics of Aldehydes and Ketones

8.1.1. Classification and Nomenclature

8.1.2. Electronic Structure of the Carbonyl Group

8.2. Nucleophilic Addition Reactions

8.2.1. Addition of Alcohols: Hemiacetal and Acetal Formation

8.2.2. Addition of Water: Hydration

8.2.3. Addition of Nitrogen Nucleophiles: Imines and Related Compounds

8.3. CH-Acidic Properties of Aldehydes and Ketones

8.3.1. Keto-Enol Tautomerism

8.3.2. The Aldol Condensation

8.3.3. The Biochemical Aldol Condensation

8.3.4. The Haloform Reaction

8.4. Oxidation and Reduction Reactions

8.4.1. Oxidation of Aldehydes and Ketones

8.4.2. Reduction of Aldehydes and Ketones

8.4.3. Biochemical Oxidation and Reduction of Carbonyl Compounds

Additional Problems

CHAPTER 9. CARBOXYLIC ACIDS AND THEIR DERIVATIVES

9.1. General Characteristics of Carboxylic Acids

9.1.1. Classification and Nomenclature

9.1.2. Electronic Structure of the Carboxyl Group

9.2. Acidic Properties

9.3. Nucleophilic Substitution at Acyl Carbon

9.3.1. Esterification of Carboxylic Acids

9.3.2. Acylation Reactions with Carboxylic Acid Derivatives

9.4. Ester Condensation

9.5. Decarboxylation of Carboxylic Acids

Additional Problems

PART 3. POLY- AND HETEROFUNCTIONAL COMPOUNDS IN LIVING SYSTEMS
CHAPTER 10. STEREOISOMERISM

10.1. Chiral and Achiral Objects

10.2. Optical Activity

10.3. Enantiomers

10.4. Configuration and the D,L Convention

10.5. Configuration and the R,S Convention

10.6. Molecules with More than One Chiral Centre

10.7. meso Compounds

10.8. Cis-trans isomerism

Additional Problems

CHAPTER 11. POLY- AND HETEROFUNCTIONAL COMPOUNDS

11.1. Types of Heterofunctional Compounds

11.2. Interaction of Different Groups in Heterofunctional Compounds

11.2.1. Intramolecular Reactions

11.2.2. Intermolecular Reactions

11.3. CH-Acidic Properties of Heterofunctional Compounds

11.3.1. Elimination Reactions

11.3.2. Keto-Enol Tautomerism

11.4. Decarboxylation of Heterofunctional Carboxylic Acids

11.5. Heterofunctional Compounds in Chemotherapy

11.5.1. Derivatives of Amino Alcohols and Amino Phenols

11.5.2. Derivatives of Amino Acids

11.5.3. Derivatives of Salicylic Acid

11.5.4. Derivatives of Sulfanilic Acid (Sulfa Drugs)

Additional Problems

CHAPTER 12. LIPIDS

12.1. Classification

12.2. Structural Components of Lipids

12.2.1. Fatty Acids

12.2.2. Alcohols

12.3. Simple Lipids

12.3.1. Waxes

12.3.2. Fats and Oils

12.3.3. Soaps and Detergents

12.4. Complex Lipids

12.4.1. Phospholipids

12.4.2. Glycolipids

Additional Problems

CHAPTER 13. TERPENOIDS AND STEROIDS

13.1. Terpenoids
13.2. Steroids

13.1.1. Structure of Steroids

13.2.2. Steroid Groups

13.2.3. General Chemical Characteristic of Steroids

Additional Problems

PART 4. BIOPOLYMERS AND THEIR STRUCTURAL CONSTITUENTS

CHAPTER 14. CARBOHYDRATES

14.1. Monosaccharides

14.1.1. Classification, Stereoisomerism, and Nomenclature

14.1.2. The Cyclic Hemiacetal Structures

14.1.3. Chemical Properties

14.2. Oligosaccharides

14.2.1. Reducing Disaccharides

14.2.2. Nonreducing Disaccharides

14.2.3. Chemical Properties

14.3. Polysaccharides

14.3.1. Homopolysaccharides

14.3.2. Heteropolysaccharides

14.4. Carbohydrates on Cell Surfaces

Additional Problems

CHAPTER 15. AMINO ACIDS, PEPTIDES, AND PROTEINS

15.1. Amino Acids

15.1.1. Structure and Classification

15.1.2. Chemical Properties

15.1.3. Biologically Important Reactions

15.2. Peptides and Proteins

15.2.1. Primary Structure

15.2.2. Secondary Structure

15.2.3. Tertiary Structure

15.2.4. Hydrolysis of Peptides and Proteins

Additional Problems

CHAPTER 16. BIOLOGICALLY ACTIVE HETEROCYCLIC COMPOUNDS

16.1. General Characteristics of Heterocyclic Systems

16.1.1. Classification

16.1.2. Nomenclature

16.2. General Aspects of Reactivity of Aromatic Heterocycles

16.2.1. Aromaticity of Pyridine and Pyrrole

16.2.2. Basicity and Acidity

16.2.3. Substitution Reactions in Heterocycles

16.3. Five-Membered Rings with One Nitrogen
16.4. Six-Membered Rings with One Heteroatom

16.4.1. Nitrogen-Containing Heterocycles

16.4.2. Oxygen-Containing Heterocycles

16.5. Rings with More than One Heteroatom

16.5.1. Imidazole and Pyrazole

16.5.2. Pyrimidine Derivatives

16.5.3. Purine Derivatives

16.6. Alkaloids

16.6.1. Pyridine Alkaloids

16.6.2. Quinoline and Isoquinoline Alkaloids

16.6.3. Tropane Alkaloids

Additional Problems

CHAPTER 17. NUCLEOTIDES AND NUCLEIC ACIDS

17.1. Constituents of Nucleic Acids

17.1.1. Structure of Nucleosides and Nucleotides

17.1.2. Some Chemical Properties of Nucleosides and Nucleotides

17.2. Primary Structure of Nucleic Acids

17.3. Secondary Structure of Nucleic Acids

17.4. Nucleoside Phosphates in Biological Processes

17.4.1. Nucleoside Polyphosphates

17.4.2. Nucleotide Coenzymes

Additional Problems

Appendix 1. PRINCIPAL PARAMETERS OF COVALENT BONDS

Appendix 2. GLOSSARY

Appendix 3. ANSWERS TO PROBLEMS

References

Subject Index
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