Holdings: The organic chemistry of enzyme-catalyzed reactions

The organic chemistry of enzyme-catalyzed reactions:

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Bibliographic Details
Main Author:	Silverman, Richard B. (Author)
Format:	Book
Language:	English
Published:	San Diego ; Amsterdam [u.a.] Academic Press 2002
Edition:	Rev. ed.
Subjects:	Biokatalyse Enzymen Organische verbindingen Reactiekinetiek Enzymes Organic reaction mechanisms Enzymkatalyse Organische Synthese
Online Access:	Inhaltsverzeichnis
Item Description:	Includes bibliographical references and index
Physical Description:	xvii, 717 p. ill. : 24 cm
ISBN:	0126437319 9780126437317

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MARC


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245	1	0	\|a The organic chemistry of enzyme-catalyzed reactions \|c Richard B. Silverman
246	1	3	\|a The organic chemistry of enzyme catalyzed reactions
250			\|a Rev. ed.
264		1	\|a San Diego ; Amsterdam [u.a.] \|b Academic Press \|c 2002
300			\|a xvii, 717 p. \|b ill. : 24 cm
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adam_text	Contents Preface Xlii About the Author xvii Enzymes as Catalysts I. What Are Enzymes, and How Do They Work? 1 Л. Historical 1 B. Specificity of Enzyme-Catalyzed Reactions 4 C. Rate Acceleration 13 II. Mechanisms of Enzyme Catalysis 15 A. Approximation 16 B. Covalent Catalysis 18 С General Acid/Base Catalysis 20 D. Electrostatic Catalysis 28 E. Derivation 30 F. Strain or Distortion 30 III. Enzyme Catalysis in Organic Media 33 IV. Enzyme Nomenclature 34 V. Epilogue 35 References 36 2 Group Transfer Reactions: Hydrolysis, Amination, Phosphorylation I. Hydrolysis Reactions 39 A. Amide Hydrolysis: Peptidases 39 B. Ester Hydrolysis: Esterases and Upases 60 II. Aminations 64 A. Glutamine-Dependent Enzymes 64 B. Aspartic Acid as a Source of Ammonia 76 vii viii Contents III. Phosphorylations: Transfers of Phosphate and Phosphate Esters to Water or Other Acceptors 76 A. Phosphatases 79 B. Phosphodiesterases 85 C. Kinases 87 References 90 3 Reduction and Oxidation I. General 95 II. Redox without a Coenzyme 95 III. Redox Reactions That Require Coenzymes 100 A. Nicotinamide Coenzymes (Pyridine Nucleotides) 100 B. Flavin Coenzymes 119 С Quinone-Containing Coenzymes 147 D. Other Redox Enzymes 157 References 169 4 Monooxygenation I. General 175 II. Flavin-Dependent Hydroxylases 175 A. No Reducing Agent Required 175 B. Hydroxylases Requiring an External Reducing Agent 177 HI. Pterin-Dependent Hydroxylases 188 A. General 188 B. Mechanism 189 IV. Heme-Dependent Monooxygenases 193 A. General № B. Molecular Oxygen Activation 196 C. Mechanistic Considerations 198 V. Nonheme Iron Oxygénation 218 A. Methane Monooxygenase 218 VI. Copper-Dependent Oxygénation 219 A. Dopamine/8-Monooxygenase 219 References 223 5 Dioxygenation I. General 227 II. Intramolecular Dioxygenases 227 A. Catechol Dioxygenases 227 B. Prostaglandin H Synthase (Cyclooxygenase) 232 Contents ix III. Intermolecular Dioxygenases 239 Α. α -Keto Acid-Dependent Dioxygenases 239 References 248 6 Substitutions I. SN1 251 A. Farnesyl Diphosphate Synthase and Related Enzymes 251 II. SnI/S^ 257 A. Disaccharide Phosphorylases 257 B. jS-Glycosidases 260 III. SN2 262 IV. SN2 265 V. SfjAr: Nucleophilic Aromatic Substitution 268 VI. Electrophilic Substitution (Addition/Elimination) 273 VII. Electrophilic Aromatic Substitution 282 References 286 7 Carboxylations I. General Concepts 289 II. Carbon Dioxide as the Carboxylating Agent 290 A. Phosphoenolpyruvate (PEP) Carboxykinase 290 B. Phosphoenolpyruvate Carboxytransphosphorylase 293 C. Vitamin K-Dependent Carboxylation of Proteins 297 III. Bicarbonate as the Carboxylating Agent 303 A. Phosphoenolpyruvate Carboxylase 303 B. Biotin-Dependent Carboxylases 307 References 319 8 Decarboxylation I. General 321 II./8-Keto Acids 321 A. Schiff Base Mechanism 323 B. Metal Ion-Catalyzed Mechanism 327 III. /J-Hydroxy Acids 329 A. Isocitrate Dehydrogenase 329 B. o-Phosphogluconate Dehydrogenase 330 IV. α -Keto Acids 331 A. General 331 B. Chemistry and Properties of Thiamin Diphosphate 331 C. Mechanism of Thiamin Diphosphate-Dependent Enzymes 335 χ Contents V. Amino Acids 343 A. Pyridoxal Phosphate-Dependent Decarboxybtion 343 B. Pyruvoyl-Dependent Decarboxylation 348 VI. Other Substrates 349 A. Orotidine 5 -Monophosphate 349 B. Mevalonate Diphosphate 354 References 356 9 Isomerizations I. General 359 II. [Ul-Hydrogen Shift 359 A. Amino Acid Racemases That Require No Cofactors 359 B. Amino Acid Racemases That Require Pyridoxal S -Phosphate 364 С Other Racemases 367 D. Epimerases 369 HI. [1,21-Hydrogen Shift 376 A. Aldose—Ketose Isomerases 376 IV. [1,31-Hydrogen Shift 378 A. Enolization 378 B. Allylic isomerizations 379 C. Aza-Allylic Isomerizations 387 V. Cis/ Trans Isomerizations 390 A. Maleylacecoaceuce homerase 390 B. Retinol Isomerase 391 С Catalytic Antibody-Catalyzed Cis/Trans Isomerization 393 VI. Phosphate Isomerization 393 References 395 10 Eliminations and Additions I. Anti Eliminations and Additions 399 A. Dehydratases and Hydratases 399 B. Elimination of Phosphate 420 C. Ammonia Lyases: Elimination of Ammonia 424 II. Syn Eliminations and Additions 428 A. Schiff Base Mechanism 429 B. Pyridoxal S -Phosphate-Dependent Eliminations 430 C. Pyridoxamine 5 -Phosphate and Iron—Sulfur Cluster-Dependent Reactions 445 D. A Catalytic Antibody-Catalyzed Syn Elimination 448 References 449 11 Aldol and Claisen Reactions and Retroreactions I. Aldol Reactions 453 A. General Chemical Considerations 453 B. Aldolases 454 Contents xi С. Porphobilinogen Synthase (5-Aminolevulinate Dehydratase) 458 D. ATP Citrate-Lyase 464 E. Transketolase 467 F. Dehydroquinate Synthase 468 II. Claisen Reactions 471 Л. General 471 B. Thiolase 472 С. Kynureninase 474 References 476 12 Formylations, Hydroxymethylations, and Methylations I. Tetrahydrofolate-Dependent Enzymes: The Transfer of One-Carbon Units 479 A. Formation of the Active Coenzyme 479 B. Transfer of One-Carbon Units 483 II. S-Adenosylmethionine-Dependent Enzymes: The Transfer of Methyl Groups 500 References 502 13 Reanangements I. Pericyclic Reactions 505 A. Sigmatropic Rearrangements 505 B. Cycloaddition Reactions 511 II. Rearrangements That Proceed via Carbenium Ion Intermediates 516 A. Acyloin Rearrangement 516 B. Cydizations 518 III. Rearrangements That Proceed via Radical Intermediates 526 A. DNA Photolyase, Formally a [2+2] Cydoreversion Reaction 526 B. Coenzyme Bu-Dependent and Related Rearrangements 530 IV. Epilogue 554 References 556 Appendix I Enzyme Kinetics 563 I. Substrate Kinetics 563 A. Michaelis-Menten Equation 563 B. Graphical Representations 567 II. Kinetics of Enzyme Inhibition 570 A. Reversible Enzyme Inhibition 570 B. Irreversible Enzyme Inhibition 584 III. Substrate Inhibition 587 IV. Nonproductive Binding 589 xii Contents V. Competing Substrates · 590 VI. Multisubstrate Systems 591 A. Sequential Mechanisms 591 VII. AUosterism and Cooperativity 593 A. General 593 B. Monod-Wyman-Changeux (MWC) Concerted Model 594 С Koshland-Némethy-Filmer (KNF) Sequential Model 595 General References 596 References 596 Appendix II Problems and Solutions 597 I. Problems 597 A. Chapter 1 597 B. Chapter 2 600 С Chapter 3 604 D. Chapter 4 605 E. Chapter 5 608 F. Chapter 6 611 G. Chapter 7 613 H. Chapter 8 614 I. Chapter 9 616 J. Chapter 10 617 K. Chapter 11 620 L. Chapter 12 622 M. Chapter 13 623 N. Biosynthetic Pathways 624 II. Solutions to Problems 626 A. Chapter 1 626 B. Chapter 2 631 С Chapter 3 636 D. Chapter 4 643 E. Chapter 5 650 F. Chapter 6 655 G. Chapter 7 657 H. Chapter 8 662 I. Chapter 9 667 J. Chapter 10 672 K. Chapter 11 681 L. Chapter 12 686 M. Chapter 13 688 N. Biosynthetic Pathways 691 Index 647
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spelling	Silverman, Richard B. Verfasser aut The organic chemistry of enzyme-catalyzed reactions Richard B. Silverman The organic chemistry of enzyme catalyzed reactions Rev. ed. San Diego ; Amsterdam [u.a.] Academic Press 2002 xvii, 717 p. ill. : 24 cm txt rdacontent n rdamedia nc rdacarrier Includes bibliographical references and index Biokatalyse gtt Enzymen gtt Organische verbindingen gtt Reactiekinetiek gtt Enzymes Organic reaction mechanisms Enzymkatalyse (DE-588)4152480-9 gnd rswk-swf Organische Synthese (DE-588)4075695-6 gnd rswk-swf Organische Synthese (DE-588)4075695-6 s Enzymkatalyse (DE-588)4152480-9 s DE-604 Digitalisierung UB Bayreuth application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009884214&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis
spellingShingle	Silverman, Richard B. The organic chemistry of enzyme-catalyzed reactions Biokatalyse gtt Enzymen gtt Organische verbindingen gtt Reactiekinetiek gtt Enzymes Organic reaction mechanisms Enzymkatalyse (DE-588)4152480-9 gnd Organische Synthese (DE-588)4075695-6 gnd
subject_GND	(DE-588)4152480-9 (DE-588)4075695-6
title	The organic chemistry of enzyme-catalyzed reactions
title_alt	The organic chemistry of enzyme catalyzed reactions
title_auth	The organic chemistry of enzyme-catalyzed reactions
title_exact_search	The organic chemistry of enzyme-catalyzed reactions
title_full	The organic chemistry of enzyme-catalyzed reactions Richard B. Silverman
title_fullStr	The organic chemistry of enzyme-catalyzed reactions Richard B. Silverman
title_full_unstemmed	The organic chemistry of enzyme-catalyzed reactions Richard B. Silverman
title_short	The organic chemistry of enzyme-catalyzed reactions
title_sort	the organic chemistry of enzyme catalyzed reactions
topic	Biokatalyse gtt Enzymen gtt Organische verbindingen gtt Reactiekinetiek gtt Enzymes Organic reaction mechanisms Enzymkatalyse (DE-588)4152480-9 gnd Organische Synthese (DE-588)4075695-6 gnd
topic_facet	Biokatalyse Enzymen Organische verbindingen Reactiekinetiek Enzymes Organic reaction mechanisms Enzymkatalyse Organische Synthese
url	http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009884214&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA
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