Organic Chemistry of Enzyme-Catalyzed Reactions, Revised Edition

By: Richard B. Silverman

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Hardcover | 28 February 2002 | Edition Number 2

At a Glance

Hardcover
736 Pages

Edition Type
Revised

Dimensions(cm)
23.11 x 15.75 x 5.33

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The Organic Chemistry of Enzyme-Catalyzed Reactions is not a book on enzymes, but rather a book on the general mechanisms involved in chemical reactions involving enzymes. An enzyme is a protein molecule in a plant or animal that causes specific reactions without itself being permanently altered or destroyed.

This is a revised edition of a very successful book, which appeals to both academic and industrial markets.

Illustrates the organic mechanism associated with each enzyme-catalyzed reaction
Makes the connection between organic reaction mechanisms and enzyme mechanisms
Compiles the latest information about molecular mechanisms of enzyme reactions
Accompanied by clearly drawn structures, schemes, and figures
Includes an extensive bibliography on enzyme mechanisms covering the last 30 years
Explains how enzymes can accelerate the rates of chemical reactions with high specificity
Provides approaches to the design of inhibitors of enzyme-catalyzed reactions
Categorizes the cofactors that are appropriate for catalyzing different classes of reactions
Shows how chemical enzyme models are used for mechanistic studies
Describes catalytic antibody design and mechanism
Includes problem sets and solutions for each chapter
Written in an informal and didactic style

Industry Reviews

Praise for the First Edition "Silverman's newest contribution will serve as an outstanding text and reference on the reaction mechanisms of enzymes. ... His treatment of the topic should also appeal to a broad range of organic, medicinal, and biological chemists who desire an up-to-date and succinct overview of the field. Silverman should be congratulated ... should quickly become the standard for mechanistic studies." --JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

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Preface	p. xiii
About the Author	p. xvii
Enzymes as Catalysts
What Are Enzymes, and How Do They Work?	p. 1
Historical	p. 1
Specificity of Enzyme-Catalyzed Reactions	p. 4
Rate Acceleration	p. 13
Mechanisms of Enzyme Catalysis	p. 15
Approximation	p. 16
Covalent Catalysis	p. 18
General Acid/Base Catalysis	p. 20
Electrostatic Catalysis	p. 28
Desolvation	p. 30
Strain or Distortion	p. 30
Enzyme Catalysis in Organic Media	p. 33
Enzyme Nomenclature	p. 34
Epilogue	p. 35
References	p. 36
Group Transfer Reactions: Hydrolysis, Amination, Phosphorylation
Hydrolysis Reactions	p. 39
Amide Hydrolysis: Peptidases	p. 39
Ester Hydrolysis: Esterases and Lipases	p. 60
Aminations	p. 64
Glutamine-Dependent Enzymes	p. 64
Aspartic Acid as a Source of Ammonia	p. 76
Phosphorylations: Transfers of Phosphate and Phosphate Esters to Water or Other Acceptors	p. 76
Phosphatases	p. 79
Phosphodiesterases	p. 85
Kinases	p. 87
References	p. 90
Reduction and Oxidation
General	p. 95
Redox without a Coenzyme	p. 95
Redox Reactions That Require Coenzymes	p. 100
Nicotinamide Coenzymes (Pyridine Nucleotides)	p. 100
Flavin Coenzymes	p. 119
Quinone-Containing Coenzymes	p. 147
Other Redox Enzymes	p. 157
References	p. 169
Monooxygenation
General	p. 175
Flavin-Dependent Hydroxylases	p. 175
No Reducing Agent Required	p. 175
Hydroxylases Requiring an External Reducing Agent	p. 177
Pterin-Dependent Hydroxylases	p. 188
General	p. 188
Mechanism	p. 189
Heme-Dependent Monooxygenases	p. 193
General	p. 193
Molecular Oxygen Activation	p. 196
Mechanistic Considerations	p. 198
Nonheme Iron Oxygenation	p. 218
Methane Monooxygenase	p. 218
Copper-Dependent Oxygenation	p. 219
Dopamine [beta]-Monooxygenase	p. 219
References	p. 223
Dioxygenation
General	p. 227
Intramolecular Dioxygenases	p. 227
Catechol Dioxygenases	p. 227
Prostaglandin H Synthase (Cyclooxygenase)	p. 232
Intermolecular Dioxygenases	p. 239
[alpha]-Keto Acid-Dependent Dioxygenases	p. 239
References	p. 248
Substitutions
S[subscript N]1	p. 251
Farnesyl Diphosphate Synthase and Related Enzymes	p. 251
S[subscript N]1/S[subscript N]2	p. 257
Disaccharide Phosphorylases	p. 257
[beta]-Glycosidases	p. 260
S[subscript N]2	p. 262
S[subscript N]2'	p. 265
S[subscript N]Ar: Nucleophilic Aromatic Substitution	p. 268
Electrophilic Substitution (Addition/Elimination)	p. 273
Electrophilic Aromatic Substitution	p. 282
References	p. 286
Carboxylations
General Concepts	p. 289
Carbon Dioxide as the Carboxylating Agent	p. 290
Phosphoenolpyruvate (PEP) Carboxykinase	p. 290
Phosphoenolpyruvate Carboxytransphosphorylase	p. 293
Vitamin K-Dependent Carboxylation of Proteins	p. 297
Bicarbonate as the Carboxylating Agent	p. 303
Phosphoenolpyruvate Carboxylase	p. 303
Biotin-Dependent Carboxylases	p. 307
References	p. 319
Decarboxylation
General	p. 321
[beta]-Keto Acids	p. 321
Schiff Base Mechanism	p. 323
Metal Ion-Catalyzed Mechanism	p. 327
[beta]-Hydroxy Acids	p. 329
Isocitrate Dehydrogenase	p. 329
6-Phosphogluconate Dehydrogenase	p. 330
[alpha]-Keto Acids	p. 331
General	p. 331
Chemistry and Properties of Thiamin Diphosphate	p. 331
Mechanism of Thiamin Diphosphate-Dependent Enzymes	p. 335
Amino Acids	p. 343
Pyridoxal Phosphate-Dependent Decarboxylation	p. 343
Pyruvoyl-Dependent Decarboxylation	p. 348
Other Substrates	p. 349
Orotidine 5'-Monophosphate	p. 349
Mevalonate Diphosphate	p. 354
References	p. 356
Isomerizations
General	p. 359
[1,1]-Hydrogen Shift	p. 359
Amino Acid Racemases That Require No Cofactors	p. 359
Amino Acid Racemases That Require Pyridoxal 5'-Phosphate	p. 364
Other Racemases	p. 367
Epimerases	p. 369
[1,2]-Hydrogen Shift	p. 376
Aldose-Ketose Isomerases	p. 376
[1,3]-Hydrogen Shift	p. 378
Enolization	p. 378
Allylic Isomerizations	p. 379
Aza-Allylic Isomerizations	p. 387
Cis/Trans Isomerizations	p. 390
Maleylacetoacetate Isomerase	p. 390
Retinol Isomerase	p. 391
Catalytic Antibody-Catalyzed Cis/Trans Isomerization	p. 393
Phosphate Isomerization	p. 393
References	p. 395
Eliminations and Additions
Anti Eliminations and Additions	p. 399
Dehydratases and Hydratases	p. 399
Elimination of Phosphate	p. 420
Ammonia Lyases: Elimination of Ammonia	p. 424
Syn Eliminations and Additions	p. 428
Schiff Base Mechanism	p. 429
Pyridoxal 5'-Phosphate-Dependent Eliminations	p. 430
Pyridoxamine 5'-Phosphate and Iron-Sulfur Cluster-Dependent Reactions	p. 445
A Catalytic Antibody-Catalyzed Syn Elimination	p. 448
References	p. 449
Aldol and Claisen Reactions and Retroreactions
Aldol Reactions	p. 453
General Chemical Considerations	p. 453
Aldolases	p. 454
Porphobilinogen Synthase (5-Aminolevulinate Dehydratase)	p. 458
ATP Citrate-Lyase	p. 464
Transketolase	p. 467
Dehydroquinate Synthase	p. 468
Claisen Reactions	p. 471
General	p. 471
Thiolase	p. 472
Kynureninase	p. 474
References	p. 476
Formylations, Hydroxymethylations, and Methylations
Tetrahydrofolate-Dependent Enzymes: The Transfer of One-Carbon Units	p. 479
Formation of the Active Coenzyme	p. 479
Transfer of One-Carbon Units	p. 483
S-Adenosylmethionine-Dependent Enzymes: The Transfer of Methyl Groups	p. 500
References	p. 502
Rearrangements
Pericyclic Reactions	p. 505
Sigmatropic Rearrangements	p. 505
Cycloaddition Reactions	p. 511
Rearrangements That Proceed via Carbenium Ion Intermediates	p. 516
Acyloin Rearrangement	p. 516
Cyclizations	p. 518
Rearrangements That Proceed via Radical Intermediates	p. 526
DNA Photolyase, Formally a [2+2] Cycloreversion Reaction	p. 526
Coenzyme B[subscript 12]-Dependent and Related Rearrangements	p. 530
Epilogue	p. 554
References	p. 556
Enzyme Kinetics	p. 563
Substrate Kinetics	p. 563
Michaelis-Menten Equation	p. 563
Graphical Representations	p. 567
Kinetics of Enzyme Inhibition	p. 570
Reversible Enzyme Inhibition	p. 570
Irreversible Enzyme Inhibition	p. 584
Substrate Inhibition	p. 587
Nonproductive Binding	p. 589
Competing Substrates	p. 590
Multisubstrate Systems	p. 591
Sequential Mechanisms	p. 591
Allosterism and Cooperativity	p. 593
General	p. 593
Monod-Wyman-Changeux (MWC) Concerted Model	p. 594
Koshland-Nemethy-Filmer (KNF) Sequential Model	p. 595
General References	p. 596
References	p. 596
Problems and Solutions	p. 597
Problems	p. 597
Chapter 1	p. 597
Chapter 2	p. 600
Chapter 3	p. 604
Chapter 4	p. 605
Chapter 5	p. 608
Chapter 6	p. 611
Chapter 7	p. 613
Chapter 8	p. 614
Chapter 9	p. 616
Chapter 10	p. 617
Chapter 11	p. 620
Chapter 12	p. 622
Chapter 13	p. 623
Biosynthetic Pathways	p. 624
Solutions to Problems	p. 626
Chapter 1	p. 626
Chapter 2	p. 631
Chapter 3	p. 636
Chapter 4	p. 643
Chapter 5	p. 650
Chapter 6	p. 655
Chapter 7	p. 657
Chapter 8	p. 662
Chapter 9	p. 667
Chapter 10	p. 672
Chapter 11	p. 681
Chapter 12	p. 686
Chapter 13	p. 688
Biosynthetic Pathways	p. 691
Index	p. 697
Table of Contents provided by Syndetics. All Rights Reserved.

Organic Chemistry of Enzyme-Catalyzed Reactions, Revised Edition

At a Glance

Hardcover

Industry Reviews

Shipping

How to return your order

Defective items

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