ORGANIC CHEMISTRY OF ENZYME-CATALYZED REACTIONS, REVISED EDITION
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By Richard Silverman, Ph.D Organic Chemistry, Northwestern University Department of Chemistry Department of Biochemistry, Molecular Biology, and Cell Biology Drug Discovery Program
Description 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.
Audience
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.
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
References
Group Transfer Reactions: Hydrolysis, Amination, Phosphorylation
I. Hydrolysis Reactions
II. Aminations
III. Phosphorylations: Transfers of Phosphate and Phosphate Esters to Water or Other
Acceptors
References
Reduction and Oxidation
I. General
II. Redox without a Coenzyme
III. Redox Reactions That Require
Coenzymes
References
Monooxygenation
I. General
II. Flavin-Dependent Hydroxylases
III. Pterin-Dependent Hydroxylases
IV. Heme-Dependent Monooxygenases
V. Nonheme Iron Oxygenation
VI. Copper-Dependent Oxygenation
References
Dioxygenation
I. General
II. Intramolecular Dioxygenases
III. Intermolecular Dioxygenases
References
Substitutions
I. SN1
II. SN1/SN2
III. SN2
IV. SN29
V. SNAr: Nucleophilic Aromatic Substitution
VI. Electrophilic Substitution (Addition/Elimination)
VII. Electrophilic
Aromatic Substitution
References
Carboxylations
I. General Concepts
II. Carbon Dioxide as the Carboxylating Agent
III. Bicarbonate as the Carboxylating Agent
References
Decarboxylation
I. General
II. b-Keto Acids
III. b-Hydroxy
Acids
IV. a-Keto Acids
V. Amino Acids
VI. Other Substrates
References
Isomerizations
I. 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 Additions
I. Anti Eliminations and Additions
II. Syn Eliminations and Additions
References
Aldol and Claisen
Reactions and Retroreactions
I. Aldol Reactions
II. Claisen Reactions
References
Formylations, Hydroxymethylations,
and Methylations
I. Tetrahydrofolate-Dependent Enzymes: The Transfer of One-Carbon Units
II. S-Adenosylmethionine-Dependent
Enzymes: The Transfer of Methyl Groups
References
Rearrangements
I. Pericyclic Reactions
II. Rearrangements That
Proceed via Carbenium Ion Intermediates
III. Rearrangements That Proceed via Radical Intermediates
IV. Epilogue
References
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
References
Appendix II Problems and Solutions
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