Organic Chemistry of Enzyme-Catalyzed Reactions, Revised Edition
- 2nd Edition - February 28, 2002
- Latest edition
- Author: Richard B. Silverman
- Language: English
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.… Read more
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
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
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
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
- Edition: 2
- Latest edition
- Published: February 28, 2002
- Language: English
RS
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, USARead Organic Chemistry of Enzyme-Catalyzed Reactions, Revised Edition on ScienceDirect