Introduction to Enzyme and Coenzyme Chemistry

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  • Edition: 3rd
  • Format: Paperback
  • Copyright: 2012-08-13
  • Publisher: Wiley

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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, and medicinal chemistry, chemical biology, biochemistry, and biotechnology.

Table of Contents

Prefacep. ix
Representation of Protein Three-Dimensional Structuresp. x
From Jack Beans to Designer Genesp. 1
Introductionp. 1
The discovery of enzymesp. 1
The discovery of coenzymesp. 3
The commercial importance of enzymes in biosynthesis and biotechnologyp. 3
The importance of enzymes as targets for drug discoveryp. 6
All Enzymes Are Proteinsp. 7
Introductionp. 7
The structures of the L--amino acidsp. 7
The primary structure of polypeptidesp. 9
Alignment of amino acid sequencesp. 11
Secondary structures found in proteinsp. 12
The folded tertiary structure of proteinsp. 15
Enzyme structure and functionp. 17
Metallo-enzymesp. 20
Membrane-associated enzymesp. 21
Glycoproteinsp. 23
Enzymes Are Wonderful Catalystsp. 26
Introductionp. 26
A thermodynamic model of catalysisp. 28
Proximity effectsp. 30
The importance of transition state stabilizationp. 32
Acid/base catalysis in enzymatic reactionsp. 36
Nucleophilic catalysis in enzymatic reactionsp. 40
The use of strain energy in enzyme catalysisp. 44
Desolvation of substrate and active site nucleophilesp. 45
Catalytic perfectionp. 46
The involvement of protein dynamics in enzyme catalysisp. 47
Methods for Studying Enzymatic Reactionsp. 50
Introductionp. 50
Enzyme purificationp. 50
Enzyme kineticsp. 52
The stereochemical course of an enzymatic reactionp. 59
The existence of intermediates in enzymatic reactionsp. 64
Analysis of transition states in enzymatic reactionsp. 68
Determination of active site catalytic groupsp. 71
Hydrolytic and Group Transfer Enzymesp. 77
Introductionp. 77
The peptidasesp. 79
CASE STUDY: HIV-1 proteasep. 90
Esterases and lipasesp. 92
Acyl transfer reactions in biosynthesis (coenzyme A)p. 93
Enzymatic phosphoryl transfer reactionsp. 95
Adenosine 5'-triphosphate (ATP)p. 101
Enzymatic glycosyl transfer reactionsp. 102
Methyl group transfer: use of S-adenosyl methionine and tetrahydrofolate coenzymes for one-carbon transfersp. 107
Enzymatic Redox Chemistryp. 115
Introductionp. 115
Nicotinamide adenine dinucleotide-dependent dehydrogenasesp. 117
Flavin-dependent dehydrogenases and oxidasesp. 122
Flavin-dependent mono-oxygenasesp. 128
CASE STUDY: Glutathione and trypanothione reductasesp. 129
Deazaflavins and pterinsp. 133
Iron-sulphur clustersp. 135
Metal-dependent mono-oxygenasesp. 136
-Ketoglutarate-dependent dioxygenasesp. 140
Non-heme iron-dependent dioxygenasesp. 141
Enzymatic Carbon-Carbon Bond Formationp. 148
Introductionp. 148
Carbon-carbon bond formation via carbanion equivalentsp. 149
Aldolasesp. 149
CASE STUDY: Fructose 1,6-bisphosphate aldolasep. 150
Claisen enzymesp. 153
Assembly of fatty acids and polyketidesp. 156
Carboxylases: Use of biotinp. 158
Ribulose bisphosphate carboxylase/oxygenase (Rubisco)p. 161
Vitamin K-dependent carboxylasep. 163
Thiamine pyrophosphate-dependent enzymesp. 165
Carbon-carbon bond formation via carbocation intermediatesp. 168
Terpene cyclasesp. 168
Carbon-carbon formation through radical intermediatesp. 173
Phenolic radical couplingsp. 173
Enzymatic Addition/Elimination Reactionsp. 181
Introductionp. 181
Hydratases and dehydratasesp. 182
Ammonia lyasesp. 187
Elimination of phosphate and pyrophosphatep. 190
CASE STUDY: 5-Enolpyravyl shikimate 3-phosphate (EPSP) synthasep. 191
Enzymatic Transformations of Amino Acidsp. 197
Introductionp. 197
Pyridoxal 5'-phosphate-dependent reactions at the -positionp. 197
CASE STUDY: Aspartate aminotransferasep. 201
Reactions at the -and -positions of amino acidsp. 204
Serine hydroxymethyltransferasep. 206
N-Pyruvoyl-dependent amino acid decarboxylasesp. 208
Imines and enamines in alkaloid biosynthesisp. 208
Isomerasesp. 213
Introductionp. 213
Cofactor-independent racemases and epimerasesp. 213
Keto-enol tautomerasesp. 216
Allylic isomerasesp. 217
CASE STUDY: Chorisrnate mutasep. 219
Radicals in Enzyme Catalysisp. 225
Introductionp. 225
Vitamin B12-dependent rearrangementsp. 225
The involvement of protein radicals in enzyme catalysisp. 229
S-adenosyl-methionine-dependent radical reactionsp. 232
Biotin synthase and sulphur insertion reactionsp. 233
Radical chemistry in DNA repair enzymesp. 234
Oxidised amino acid cofactors and quinoproteinsp. 238
Non-Enzymatic Biological Catalysisp. 242
Introductionp. 242
Catalytic RNAp. 242
Catalytic antibodiesp. 246
Synthetic enzyme modelsp. 251
Cahn-Ingold-Prelog Rule for Stereochemical Nomenclaturep. 258
Amino Acid Abbreviationsp. 260
A Simple Demonstration of Enzyme Catalysisp. 261
Answers to Problemsp. 263
Indexp. 271
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