Organic Chemistry of Enzyme-Catalyzed Reactions, Revised Edition


  • Richard B. Silverman, Ph.D Organic Chemistry, Northwestern University, Evanston, IL, USA

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.
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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.


Book information

  • Published: February 2002
  • ISBN: 978-0-12-643731-7


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

Table of Contents

Enzymes as CatalystsI. What Are Enzymes, and How Do They Work? II. Mechanisms of Enzyme CatalysisIII. Enzyme Catalysis in Organic MediaIV. Enzyme NomenclatureV. EpilogueReferencesGroup Transfer Reactions: Hydrolysis, Amination, Phosphorylation I. Hydrolysis ReactionsII. AminationsIII. Phosphorylations: Transfers of Phosphate and Phosphate Esters to Water or Other AcceptorsReferencesReduction and OxidationI. GeneralII. Redox without a CoenzymeIII. Redox Reactions That Require CoenzymesReferencesMonooxygenationI. GeneralII. Flavin-Dependent HydroxylasesIII. Pterin-Dependent HydroxylasesIV. Heme-Dependent MonooxygenasesV. Nonheme Iron OxygenationVI. Copper-Dependent OxygenationReferencesDioxygenationI. GeneralII. Intramolecular DioxygenasesIII. Intermolecular DioxygenasesReferencesSubstitutionsI. SN1II. SN1/SN2 III. SN2 IV. SN29 V. SNAr: Nucleophilic Aromatic SubstitutionVI. Electrophilic Substitution (Addition/Elimination)VII. Electrophilic Aromatic Substitution References CarboxylationsI. General Concepts II. Carbon Dioxide as the Carboxylating Agent III. Bicarbonate as the Carboxylating Agent References DecarboxylationI. General II. b-Keto Acids III. b-Hydroxy Acids IV. a-Keto Acids V. Amino Acids VI. Other Substrates References IsomerizationsI. General II. [1,1]-Hydrogen Shift III. [1,2]-Hydrogen Shift IV. [1,3]-Hydrogen Shift V. Cis/Trans Isomerizations VI. Phosphate Isomerization References Eliminations and AdditionsI. Anti Eliminations and Additions II. Syn Eliminations and Additions References Aldol and Claisen Reactions and RetroreactionsI. Aldol Reactions II. Claisen Reactions References Formylations, Hydroxymethylations, and MethylationsI. Tetrahydrofolate-Dependent Enzymes: The Transfer of One-Carbon Units II. S-Adenosylmethionine-Dependent Enzymes: The Transfer of Methyl Groups References RearrangementsI. Pericyclic Reactions II. Rearrangements That Proceed via Carbenium Ion Intermediates III. Rearrangements That Proceed via Radical Intermediates IV. Epilogue References Appendix I Enzyme KineticsI. Substrate Kinetics II. Kinetics of Enzyme Inhibition III. Substrate Inhibition IV. Nonproductive Binding V. Competing Substrates VI. Multisubstrate Systems VII. Allosterism and CooperativityReferences Appendix II Problems and Solutions