Organic Chemistry of Enzyme-Catalyzed Reactions

ISBN-10: 0126437319
ISBN-13: 9780126437317
Edition: 2nd 2002 (Revised)
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Book details

List price: $131.00
Edition: 2nd
Copyright year: 2002
Publisher: Elsevier Science & Technology Books
Publication date: 2/28/2002
Binding: Hardcover
Pages: 800
Size: 6.25" wide x 9.00" long x 1.50" tall
Weight: 2.750
Language: English

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 [beta]-Monooxygenase
References
Dioxygenation
General
Intramolecular Dioxygenases
Catechol Dioxygenases
Prostaglandin H Synthase (Cyclooxygenase)
Intermolecular Dioxygenases
[alpha]-Keto Acid-Dependent Dioxygenases
References
Substitutions
S[subscript N]1
Farnesyl Diphosphate Synthase and Related Enzymes
S[subscript N]1/S[subscript N]2
Disaccharide Phosphorylases
[beta]-Glycosidases
S[subscript N]2
S[subscript N]2'
S[subscript N]Ar: Nucleophilic Aromatic Substitution
Electrophilic Substitution (Addition/Elimination)
Electrophilic Aromatic Substitution
References
Carboxylations
General Concepts
Carbon Dioxide as the Carboxylating Agent
Phosphoenolpyruvate (PEP) Carboxykinase
Phosphoenolpyruvate Carboxytransphosphorylase
Vitamin K-Dependent Carboxylation of Proteins
Bicarbonate as the Carboxylating Agent
Phosphoenolpyruvate Carboxylase
Biotin-Dependent Carboxylases
References
Decarboxylation
General
[beta]-Keto Acids
Schiff Base Mechanism
Metal Ion-Catalyzed Mechanism
[beta]-Hydroxy Acids
Isocitrate Dehydrogenase
6-Phosphogluconate Dehydrogenase
[alpha]-Keto Acids
General
Chemistry and Properties of Thiamin Diphosphate
Mechanism of Thiamin Diphosphate-Dependent Enzymes
Amino Acids
Pyridoxal Phosphate-Dependent Decarboxylation
Pyruvoyl-Dependent Decarboxylation
Other Substrates
Orotidine 5'-Monophosphate
Mevalonate Diphosphate
References
Isomerizations
General
[1,1]-Hydrogen Shift
Amino Acid Racemases That Require No Cofactors
Amino Acid Racemases That Require Pyridoxal 5'-Phosphate
Other Racemases
Epimerases
[1,2]-Hydrogen Shift
Aldose-Ketose Isomerases
[1,3]-Hydrogen Shift
Enolization
Allylic Isomerizations
Aza-Allylic Isomerizations
Cis/Trans Isomerizations
Maleylacetoacetate Isomerase
Retinol Isomerase
Catalytic Antibody-Catalyzed Cis/Trans Isomerization
Phosphate Isomerization
References
Eliminations and Additions
Anti Eliminations and Additions
Dehydratases and Hydratases
Elimination of Phosphate
Ammonia Lyases: Elimination of Ammonia
Syn Eliminations and Additions
Schiff Base Mechanism
Pyridoxal 5'-Phosphate-Dependent Eliminations
Pyridoxamine 5'-Phosphate and Iron-Sulfur Cluster-Dependent Reactions
A Catalytic Antibody-Catalyzed Syn Elimination
References
Aldol and Claisen Reactions and Retroreactions
Aldol Reactions
General Chemical Considerations
Aldolases
Porphobilinogen Synthase (5-Aminolevulinate Dehydratase)
ATP Citrate-Lyase
Transketolase
Dehydroquinate Synthase
Claisen Reactions
General
Thiolase
Kynureninase
References
Formylations, Hydroxymethylations, and Methylations
Tetrahydrofolate-Dependent Enzymes: The Transfer of One-Carbon Units
Formation of the Active Coenzyme
Transfer of One-Carbon Units
S-Adenosylmethionine-Dependent Enzymes: The Transfer of Methyl Groups
References
Rearrangements
Pericyclic Reactions
Sigmatropic Rearrangements
Cycloaddition Reactions
Rearrangements That Proceed via Carbenium Ion Intermediates
Acyloin Rearrangement
Cyclizations
Rearrangements That Proceed via Radical Intermediates
DNA Photolyase, Formally a [2+2] Cycloreversion Reaction
Coenzyme B[subscript 12]-Dependent and Related Rearrangements
Epilogue
References
Enzyme Kinetics
Substrate Kinetics
Michaelis-Menten Equation
Graphical Representations
Kinetics of Enzyme Inhibition
Reversible Enzyme Inhibition
Irreversible Enzyme Inhibition
Substrate Inhibition
Nonproductive Binding
Competing Substrates
Multisubstrate Systems
Sequential Mechanisms
Allosterism and Cooperativity
General
Monod-Wyman-Changeux (MWC) Concerted Model
Koshland-Nemethy-Filmer (KNF) Sequential Model
General References
References
Problems and Solutions
Problems
Chapter 1
Chapter 2
Chapter 3
Chapter 4
Chapter 5
Chapter 6
Chapter 7
Chapter 8
Chapter 9
Chapter 10
Chapter 11
Chapter 12
Chapter 13
Biosynthetic Pathways
Solutions to Problems
Chapter 1
Chapter 2
Chapter 3
Chapter 4
Chapter 5
Chapter 6
Chapter 7
Chapter 8
Chapter 9
Chapter 10
Chapter 11
Chapter 12
Chapter 13
Biosynthetic Pathways
Index

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