Rent 9781119995944 | Introduction to Enzyme and Coenzyme Chemistry

Summary Table of Contents

Looking at enzymes from an organic chemistry perspective, this updated reference includes information on recent advances in our understanding of enzyme action; topical examples to illustrate key points; two-color figures of the active sites of enzymes discussed in the text to illustrate the interplay between enzyme structure and function; and end-of-chapter problems to allow readers to check their understanding of the material. This concise but comprehensive guide is essential for undergraduate and postgraduate students of organic, bio-organic,... MORE

Preface	p. ix
Representation of Protein Three-Dimensional Structures	p. x
From Jack Beans to Designer Genes	p. 1
Introduction	p. 1
The discovery of enzymes	p. 1
The discovery of coenzymes	p. 3
The commercial importance of enzymes in biosynthesis and biotechnology	p. 3
The importance of enzymes as targets for drug discovery	p. 6
All E... MOREnzymes Are Proteins	p. 7
Introduction	p. 7
The structures of the L-�-amino acids	p. 7
The primary structure of polypeptides	p. 9
Alignment of amino acid sequences	p. 11
Secondary structures found in proteins	p. 12
The folded tertiary structure of proteins	p. 15
Enzyme structure and function	p. 17
Metallo-enzymes	p. 20
Membrane-associated enzymes	p. 21
Glycoproteins	p. 23
Enzymes Are Wonderful Catalysts	p. 26
Introduction	p. 26
A thermodynamic model of catalysis	p. 28
Proximity effects	p. 30
The importance of transition state stabilization	p. 32
Acid/base catalysis in enzymatic reactions	p. 36
Nucleophilic catalysis in enzymatic reactions	p. 40
The use of strain energy in enzyme catalysis	p. 44
Desolvation of substrate and active site nucleophiles	p. 45
Catalytic perfection	p. 46
The involvement of protein dynamics in enzyme catalysis	p. 47
Methods for Studying Enzymatic Reactions	p. 50
Introduction	p. 50
Enzyme purification	p. 50
Enzyme kinetics	p. 52
The stereochemical course of an enzymatic reaction	p. 59
The existence of intermediates in enzymatic reactions	p. 64
Analysis of transition states in enzymatic reactions	p. 68
Determination of active site catalytic groups	p. 71
Hydrolytic and Group Transfer Enzymes	p. 77
Introduction	p. 77
The peptidases	p. 79
CASE STUDY: HIV-1 protease	p. 90
Esterases and lipases	p. 92
Acyl transfer reactions in biosynthesis (coenzyme A)	p. 93
Enzymatic phosphoryl transfer reactions	p. 95
Adenosine 5'-triphosphate (ATP)	p. 101
Enzymatic glycosyl transfer reactions	p. 102
Methyl group transfer: use of S-adenosyl methionine and tetrahydrofolate coenzymes for one-carbon transfers	p. 107
Enzymatic Redox Chemistry	p. 115
Introduction	p. 115
Nicotinamide adenine dinucleotide-dependent dehydrogenases	p. 117
Flavin-dependent dehydrogenases and oxidases	p. 122
Flavin-dependent mono-oxygenases	p. 128
CASE STUDY: Glutathione and trypanothione reductases	p. 129
Deazaflavins and pterins	p. 133
Iron-sulphur clusters	p. 135
Metal-dependent mono-oxygenases	p. 136
�-Ketoglutarate-dependent dioxygenases	p. 140
Non-heme iron-dependent dioxygenases	p. 141
Enzymatic Carbon-Carbon Bond Formation	p. 148
Introduction	p. 148
Carbon-carbon bond formation via carbanion equivalents	p. 149
Aldolases	p. 149
CASE STUDY: Fructose 1,6-bisphosphate aldolase	p. 150
Claisen enzymes	p. 153
Assembly of fatty acids and polyketides	p. 156
Carboxylases: Use of biotin	p. 158
Ribulose bisphosphate carboxylase/oxygenase (Rubisco)	p. 161
Vitamin K-dependent carboxylase	p. 163
Thiamine pyrophosphate-dependent enzymes	p. 165
Carbon-carbon bond formation via carbocation intermediates	p. 168
Terpene cyclases	p. 168
Carbon-carbon formation through radical intermediates	p. 173
Phenolic radical couplings	p. 173
Enzymatic Addition/Elimination Reactions	p. 181
Introduction	p. 181
Hydratases and dehydratases	p. 182
Ammonia lyases	p. 187
Elimination of phosphate and pyrophosphate	p. 190
CASE STUDY: 5-Enolpyravyl shikimate 3-phosphate (EPSP) synthase	p. 191
Enzymatic Transformations of Amino Acids	p. 197
Introduction	p. 197
Pyridoxal 5'-phosphate-dependent reactions at the �-position	p. 197
CASE STUDY: Aspartate aminotransferase	p. 201
Reactions at the �-and �-positions of amino acids	p. 204
Serine hydroxymethyltransferase	p. 206
N-Pyruvoyl-dependent amino acid decarboxylases	p. 208
Imines and enamines in alkaloid biosynthesis	p. 208
Isomerases	p. 213
Introduction	p. 213
Cofactor-independent racemases and epimerases	p. 213
Keto-enol tautomerases	p. 216
Allylic isomerases	p. 217
CASE STUDY: Chorisrnate mutase	p. 219
Radicals in Enzyme Catalysis	p. 225
Introduction	p. 225
Vitamin B₁₂-dependent rearrangements	p. 225
The involvement of protein radicals in enzyme catalysis	p. 229
S-adenosyl-methionine-dependent radical reactions	p. 232
Biotin synthase and sulphur insertion reactions	p. 233
Radical chemistry in DNA repair enzymes	p. 234
Oxidised amino acid cofactors and quinoproteins	p. 238
Non-Enzymatic Biological Catalysis	p. 242
Introduction	p. 242
Catalytic RNA	p. 242
Catalytic antibodies	p. 246
Synthetic enzyme models	p. 251
Cahn-Ingold-Prelog Rule for Stereochemical Nomenclature	p. 258
Amino Acid Abbreviations	p. 260
A Simple Demonstration of Enzyme Catalysis	p. 261
Answers to Problems	p. 263
Index	p. 271
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