Chemistry of Biomolecules, Second Edition

474 Pages·2019·12.322 MB·\474

by  S. P. Bhutani (Author)

Chemistry of
Biomolecules
Second Edition

Chemistry of
Biomolecules
Second Edition
S. P. Bhutani
Formerly Associate Professor
Department of Chemistry, Rajdhani College
University of Delhi, India
CRC Press
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Library of Congress Cataloging-in-Publication Data
Names: Bhutani, S. P., author.
Title: Chemistry of biomolecules / S.P. Bhutani, Formerly Associate
Professor, Department of Chemistry, Rajdhani College, University of
Delhi, India.
Description: Second edition. | Boca Raton : CRC Press, 2019. | Includes
bibliographical references and index. | Summary: “Biomolecules are
molecules that are involved in the maintenance and metabolic processes
of all living organisms. This fully revised second edition offers
extensive coverage of important biomolecules from an organic chemistry
point of view. The author discusses carbohydrates, amino acids,
peptides, proteins, enzymes, pyrimidines, purines, nucleic acids,
terpenoids, and lipids. The various topics are described in simple,
lucid language and explain the mechanisms of the reactions wherever
required. Ideal for upper level undergraduates, graduates and
researchers”-- Provided by publisher.
Identifiers: LCCN 2019030756 | ISBN 9780367208554 (hardback) | ISBN
9780429266423 (ebook)
Subjects: LCSH: Biomolecules. | Biochemistry.
Classification: LCC QD415 .B44 2019 | DDC 572--dc23
LC record available at https://lccn.loc.gov/2019030756
Visit the Taylor & Francis Web site at
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Dedicated to my
Granddaughter
Little Princess ‘Aarna’
with
Love and Blessings

Contents
Preface xxi
1. CARBOHYDRATES 1-85
1.1 Introduction 2
1.2 Occurrence and Biological Importance 2
1.3 Definitions
1.4 Formation of Carbohydrates in Plants 3
1.5 Classification of Carbohydrates 4
A. Monosaccharides 4
B. Oligosaccharides 5
C. Polysaccharides 8
1.6 Configurational Relationship of Monosaccharides 8
A. Correlation of the Configuration of D-Glucose and
D-Glyceraldehyde 8
B. Aldotetroses 9
C. Erythro and Threo Diastereomers 10
D. Aldopentoses 11
E. Aldohexoses 12
1.7 Epimers 13
1.8 Structure and Properties of D-Glucose 15
A. Open-Chain Structure of D-Glucose 15
B. Configuration of D (+)-Glucose 17
C. Cyclic Structure of D(+)-Glucose 20
D. Conformations of D(+) Glucose 24
1.9 Determination of the Ring Size of Glucose 25
A. Evidence for the Pyranose Structure of D(+)-Glucose 25
B. Evidence for the Furanose Structure of D(+)-Glucose 26
C. Determination of Ring Size by Oxidations with
Periodic Acid 28
1.10 Mutarotation 29
1.11 Osazone Formation 31
1.12 Ketohexoses 33
1.13 Structure of D(–)-Fructose 33
viii Contents
A. Configuration of D-Fructose 34
B. Cyclic Structure of D-Fructose 35
1.14 Reactions of Monosaccharides 36
A. Esterification 36
B. Ether Formation 36
C. Formation of Glycosides 37
D. Esters of Phosphoric Acid 38
E. Oxidation of Monosaccharides 41
F. Reduction of Monosaccharides 46
1.15 Lengthening the Carbon Chain of Aldoses–The
Kiliani-Fischer Synthesis 47
1.16 Shortening the Carbon Chain of Aldoses 49
A. The Wohl Degradation 49
B. The Ruff Degradation 49
C. Weermann Degradation 50
1.17 Interconversions 51
A. The Interconversion of Glucose, Mannose and Fructose 51
B. Conversion of an Aldose to the Corresponding Ketose 51
C. Conversion of an Aldose to its Epimer 52
D. Conversion of a Ketose into the Corresponding Aldose 52
1.18 Maltose 53
1.19 Lactose 56
1.20 Cellobiose 59
1.21 Sucrose 60
1.22 Aldopentoses—The Sugars of Nucleic Acids 62
A. Deoxy Sugars 2-Deoxy-D-Ribose 62
B. D-Ribose 64
1.23 Polysaccharides 65
A. Cellulose 65
B. Starch 67
C. Glycogen 70
D. Chitin 71
E. Heparin 72
1.24 Biosynthesis of Carbohydrates—The Calvin Cycle 72
A. Stage 1 73
B. Stage 2 73
C. Stage 3 74
1.25 Natural Products Derived from Carbohydrates 76
A. Ascorbic Acid 76
B. Some Natural Glycosides 78
C. Anthocyanins—Natural Colouring Matters 79
D. Anthraquinone Glycosides 80
Contents ix
E. Indican–A Natural Colouring Matter 81
F. Cardiac Glycosides 81
G. Some Biologically Important Sugars 82
H. Glycosylamines 83
I. Amino Sugars 83
J. Carbohydrate Antibiotics 84
2. Amino Acids, Peptides, and Proteins 87-192
2.1 Introduction 88
2.2 Amino Acids – The Building Blocks of Proteins 88
2.3 Classification of Amino Acids 89
2.4 The Essential Amino Acids 92
2.5 Stereochemistry of α-Amino Acids 93
2.6 Synthesis of α-Amino Acids 93
A. Amination of α-Halogeno Acids 93
B. Gabriel Phthalimide Synthesis 95
C. Strecker Synthesis 95
D. Malonic Ester Synthesis 96
E. Aldehyde Condensations with Glycine Derivatives
(Erlenmeyer Azlactone Synthesis) 101
F. Synthesis via Molecular Rearrangements 103
G. Reductive Amination 107
H. Oxidation of Amino Alcohols 108
2.7 Resolution of Racemic Mixtures of Amino Acids 108
2.8 Stereoselective Synthesis of Amino Acids 110
2.9 Biosynthesis Amino Acids 111
2.10 Amino Acids as Dipolar ions 115
2.11 Amino Acids as Acids and Bases 116
2.12 Isoelectric Point 120
2.13 Separation of Amino Acids 124
A. Electrophoresis 124
B. Paper Chromatography 124
C. Thine layer Chromatography (TLC) 125
D. Column Chromatography 126
E. Ion-Exchange Chromatography 127
2.14 Chemical Reactions of Amino Acids 128
A. Reactions due to Amino Group 128
B. Reactions due to the Carboxyl Group 131
C. Reactions due to both the Amino and Carboxyl Groups 133
2.15 Polypeptides 136
A. Introduction 136
B. Nomenclature of Peptides 136