Wong / Whitesides Enzymes in Synthetic Organic Chemistry

1. Auflage 2013
ISBN: 978-0-08-050582-4
Verlag: Elsevier Science & Techn.
Format: PDF
Kopierschutz: 1 - PDF Watermark

E-Book, Englisch, Band Volume 12, 389 Seiten, Web PDF

Reihe: Tetrahedron Organic Chemistry

This book covers the most recent development of enzymatic organic synthesis, with particular focus on the use of isolated enzymes. It is organized into one introductory chapter dealing with the characteristics of enzymes as catalysts, and five chapters dealing with different types of chemical transformations. Methods for enzyme immobilization and stabilizaton, the use of enzymes in extreme environments, and the alteration of enzyme properties by chemical modification and site-directed mutagenesis for synthetic purposes are covered.

Autoren/Hrsg.

Wong, C. H.

Whitesides, G. M.

Inhaltsverzeichnis

1;Front Cover;1
2;Enzymes in Synthetic Organic Chemistry;4
3;Copyright Page;5
4;Table of Contents;6
5;Preface;14
6;Acknowledgements;18
7;Chapter 1. General Aspects;20
7.1;1. Rate Acceleration in Enzyme-Catalyzed Reactions;22
7.2;2. Michaelis–Menten Kinetics;23
7.3;3. Enzyme Inhibition;27
7.4;4. Specificity;28
7.5;5. Improvement or Alteration of Enzyme Specificity;32
7.6;6. Enzyme Stabilization and Reactor Configuration;36
7.7;7. Cofactor Regeneration;38
7.8;8. Enzyme Catalysis in Organic Solvents;41
7.9;9. Multienzyme Systems and Metabolic Engineering;44
7.10;10. Rational Design of New Enzymatic Catalysts;46
7.11;11. Conclusion;49
7.12;References;52
8;Chapter 2. Use of Hydrolytic Enzymes: Amidases, Proteases, Esterases, Lipases, Nitrilases, Phosphatases, Epoxide Hydrolases;60
8.1;1. Amidases;61
8.2;2. Protease-Catalyzed Peptide Synthesis;65
8.3;3. Proteases that Act as Esterases;78
8.4;4. Acetylcholine Esterase;83
8.5;5. Pig Liver Esterase;85
8.6;6. Phospholipases;88
8.7;7. Cholesterol Esterase;88
8.8;8. Lipases;89
8.9;9. Nitrile Hydrolysis Enzymes;127
8.10;10. Epoxide Hydrolase;129
8.11;11. Phosphatase;129
8.12;References;130
9;Chapter 3. Oxidoreductions;150
9.1;1. Nicotinamide Cofactor Dependent Oxidoreductions;150
9.2;2. Dehydrogenases which Utilize Ketoacids as Substrates;173
9.3;3. Other NAD(P)-Dependent Dehydrogenases;178
9.4;4. Oxidoreductases that are Metalloenzymes;181
9.5;References;202
10;Chapter 4. C–C Bond Formation;214
10.1;1. Aldol Condensation;214
10.2;2. Ketol and Aldol Transfer Reactions;248
10.3;3. Addition of HCN to Aldehydes;249
10.4;4. Acyloin Condensation;251
10.5;5. C–C Bond Forming Reactions Involving AcetylCoA;254
10.6;6. Isoprenoid and Steroid Synthesis;257
10.7;7. ß-Replacement of Chloroalanine;259
10.8;8. C–C Bond Formation Catalyzed by Vitamin B12;259
10.9;References;261
11;Chapter 5. Synthesis of Glycoside Bonds;271
11.1;1. Background;271
11.2;2. Glycosyltransferases of the Leloir Pathway;275
11.3;3. Non-Leloir Glycosyltransferases: Transfer of Glycosyl Donors from Glycosyl Phosphates and Glycosides;298
11.4;4. Glycosidases;302
11.5;5. Transglycosidases;309
11.6;6. Synthesis of N-Glycosides;309
11.7;7. Biological Applications of Synthetic Glycoconjugates;315
11.8;8. Future Opportunities;316
11.9;References;316
12;Chapter 6. Addition, Elimination and other Group Transfer Reactions (Phosphoryl-, Methyl-, Sulfo- and Amino-Transfer Reactions);331
12.1;1. Addition of Water to Alkenes: Fumarase;331
12.2;2. Addition of Ammonia to Double Bonds: Ammonia Lyases;332
12.3;3. Transamination: Aminotransferases;332
12.4;4. Addition and Elimination of the Carboxyl Group;334
12.5;5. Nucleoside Triphosphate Requiring Enzymatic Reactions;335
12.6;6. Preparation of Derivatives of ATP Chiral at the a-, ß, or .-Phosphorus;344
12.7;7. Phosphorothioate-Containing DNA and RNA (DNA-S and RNA-S);347
12.8;8. DNA and RNA Oligomers;348
12.9;9. Incorporation of Modified or Unnatural Bases into DNA or RNA;350
12.10;10. Dehalogenation;352
12.11;11. Synthesis of Chiral Methyl Groups;354
12.12;12. S-Adenosylmethionine and Transmethylation;354
12.13;13. Sulfate Activation and Transfer Reactions;357
12.14;References;360
13;Subject Index;366