Organic Chemistry of Enzyme-Catalyzed Reactions, Revised Edition - 2nd Edition - ISBN: 9780126437317

Organic Chemistry of Enzyme-Catalyzed Reactions, Revised Edition

2nd Edition

Authors: Richard B. Silverman
eBook ISBN:
eBook ISBN: 9780080513362
Hardcover ISBN: 9780126437317
Imprint: Academic Press
Published Date: 28th February 2002
Page Count: 800
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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.

Key Features

  • 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


Upper division undergraduate and graduate students in the fields of chemistry (organic and medicinal) and biochemistry. Industrial chemists working on the design of enzyme inhibitors in the pharmaceutical and agricultural industries

Table of Contents

Enzymes as Catalysts
I. What Are Enzymes, and How Do They Work?
II. Mechanisms of Enzyme Catalysis
III. Enzyme Catalysis in Organic Media
IV. Enzyme Nomenclature
V. Epilogue

Group Transfer Reactions: Hydrolysis, Amination, Phosphorylation
I. Hydrolysis Reactions
II. Aminations
III. Phosphorylations: Transfers of Phosphate and Phosphate Esters to Water or Other Acceptors

Reduction and Oxidation
I. General
II. Redox without a Coenzyme
III. Redox Reactions That Require Coenzymes

I. General
II. Flavin-Dependent Hydroxylases
III. Pterin-Dependent Hydroxylases
IV. Heme-Dependent Monooxygenases
V. Nonheme Iron Oxygenation
VI. Copper-Dependent Oxygenation

I. General
II. Intramolecular Dioxygenases
III. Intermolecular Dioxygenases

I. SN1
IV. SN29
V. SNAr: Nucleophilic Aromatic Substitution
VI. Electrophilic Substitution (Addition/Elimination)
VII. Electrophilic Aromatic Substitution

I. General Concepts
II. Carbon Dioxide as the Carboxylating Agent
III. Bicarbonate as the Carboxylating Agent

I. General
II. b-Keto Acids
III. b-Hydroxy Acids
IV. a-Keto Acids
V. Amino Acids
VI. Other Substrates

I. General
II. [1,1]-Hydrogen Shift
III. [1,2]-Hydrogen Shift
IV. [1,3]-Hydrogen Shift
V. Cis/Trans Isomerizations
VI. Phosphate Isomerization

Eliminations and Additions
I. Anti Eliminations and Additions
II. Syn Eliminations and Additions

Aldol and Claisen Reactions and Retroreactions
I. Aldol Reactions
II. Claisen Reactions

Formylations, Hydroxymethylations, and Methylations
I. Tetrahydrofolate-Dependent Enzymes: The Transfer of One-Carbon Units
II. S-Adenosylmethionine-Dependent Enzymes: The Transfer of Methyl Groups

I. Pericyclic Reactions
II. Rearrangements That Proceed via Carbenium Ion Intermediates
III. Rearrangements That Proceed via Radical Intermediates
IV. Epilogue

Appendix I Enzyme Kinetics
I. Substrate Kinetics
II. Kinetics of Enzyme Inhibition
III. Substrate Inhibition
IV. Nonproductive Binding
V. Competing Substrates
VI. Multisubstrate Systems
VII. Allosterism and Cooperativity
Appendix II Problems and Solutions


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© Academic Press 2002
Academic Press
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About the Author

Richard B. Silverman

Professor Richard B. Silverman received his B.S. degree in chemistry from The Pennsylvania State University in 1968 and his Ph.D. degree in organic chemistry from Harvard University in 1974 (with time off for a two-year military obligation from 1969-1971). After two years as a NIH postdoctoral fellow in the laboratory of the late Professor Robert Abeles in the Graduate Department of Biochemistry at Brandeis University, he joined the chemistry faculty at Northwestern University. In 1986, he became Professor of Chemistry and Professor of Biochemistry, Molecular Biology, and Cell Biology. In 2001, he became the Charles Deering McCormick Professor of Teaching Excellence for three years, and since 2004 he has been the John Evans Professor of Chemistry. His research can be summarized as investigations of the molecular mechanisms of action, rational design, and syntheses of potential medicinal agents acting on enzymes and receptors.

His awards include DuPont Young Faculty Fellow (1976), Alfred P. Sloan Research Fellow (1981-1985), NIH Research Career Development Award (1982-1987), Fellow of the American Institute of Chemists (1985), Fellow of the American Association for the Advancement of Science (1990), Arthur C. Cope Senior Scholar Award of the American Chemical Society (2003), Alumni Fellow Award from Pennsylvania State University (2008), Medicinal Chemistry Hall of Fame of the American Chemical Society (2009), the Perkin Medal from the Society of Chemical Industry (2009), the Hall of Fame of Central High School of Philadelphia (2011), the E.B. Hershberg Award for Important Discoveries in Medicinally Active Substances from the American Chemical Society (2011), Fellow of the American Chemical Society (2011), Sato Memorial International Award of the Pharmaceutical Society of Japan (2012), Roland T. Lakey Award of Wayne State University (2013), BMS-Edward E. Smissman Award of the American Chemical Society (2013), the Centenary Prize of the Royal Society of Chemistry (2013), and the Excellence in Medicinal Chemistry Prize of the Israel Chemical Society (2014).

Professor Silverman has published over 320 research and review articles, holds 49 domestic and foreign patents, and has written four books (The Organic Chemistry of Drug Design and Drug Action is translated into German and Chinese). He is the inventor of LyricaTM, a drug marketed by Pfizer for epilepsy, neuropathic pain, fibromyalgia, and spinal cord injury pain; currently, he has another CNS drug in clinical trials.

Affiliations and Expertise

Northwestern University, Evanston, IL, USA


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