The organic chemistry of enzyme-catalyzed reactions
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Bibliographic Information
The organic chemistry of enzyme-catalyzed reactions
Academic, c2000
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Includes bibliographical references and index
Description and Table of Contents
Description
Written for advanced undergraduate and graduate students as well as professionals in organic and medicinal chemistry and biochemistry, this unique text illuminates the "black box" of enzyme-catalyzed reactions by showing how enzymes are simply highly efficient organic chemists. Enzyme-catalyzed reactions are essential for the design of enzyme inhibitors in the pharmaceutical and agricultural industries, and of growing importance for process development in the chemical and biotechnology industries. Following a general introduction to the role of enzymes as catalysts, each chapter describes the organic reaction mechanisms that are used by enzymes to catalyze a particular family of organic transformations. The compilation includes a vast number of drawings to illustrate structures and mechanisms, and focuses on one or two examples of enzymes that catalyze the particular chemistry for that transformation. The Organic Chemistry of Enzyme-Catalyzed Reactions is not a book on enzymes, but rather the general mechanisms used by enzymes. Extensive references refer to the many experiments that have helped to elucidate enzyme mechanisms.
Chemical model studies as an aid in mechanistic studies are also discussed, as are the design of haptens and the generation of catalytic antibodies ("designer enzymes"). Problem sets and solutions are provided to check the reader's understanding of the principles described.
Table of Contents
Preface About the Author Enzymes as Catalysts What Are Enzymes, and How Do They Work? Historical Specificity of Enzyme-Catalyzed Reactions Rate Acceleration Mechanisms of Enzyme Catalysis Approximation Covalent Catalysis General Acid/Base Catalysis Electrostatic Catalysis Desolvation Strain or Distortion Enzyme Catalysis in Organic Media Enzyme Nomenclature Epilogue References Group Transfer Reactions: Hydrolysis, Amination, Phosphorylation Hydrolysis Reactions Amide Hydrolysis: Peptidases Ester Hydrolysis: Esterases and Lipases Aminations Glutamine-Dependent Enzymes Aspartic Acid as a Source of Ammonia Phosphorylations: Transfers of Phosphate and Phosphate Esters to Water or Other Acceptors Phosphatases Phosphodiesterases Kinases References Reduction and Oxidation General Redox without a Coenzyme Redox Reactions That Require Coenzymes Nicotinamide Coenzymes (Pyridine Nucleotides) Flavin Coenzymes Quinone-Containing Coenzymes Other Redox Enzymes References Monooxygenation General Flavin-Dependent Hydroxylases No Reducing Agent Required Hydroxylases Requiring an External Reducing Agent Pterin-Dependent Hydroxylases General Mechanism Heme-Dependent Monooxygenases General Molecular Oxygen Activation Mechanistic Considerations Nonheme Iron Oxygenation Methane Monooxygenase Copper-Dependent Oxygenation Dopamine a-Monooxygenase References Dioxygenation General Intramolecular Dioxygenases Catechol Dioxygenases Prostaglandin H Synthase (Cyclooxygenase) Intermolecular Dioxygenases a-Keto Acid-Dependent Dioxygenases
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