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.
For graduate students and other professionals involved with organic synthesis, medicinal chemistry, biochemistry, bio-organic chemistry, biotechnology and other applied biological sciences.
Enzymes in Synthetic Organic Chemistry, 1st Edition
Preface. Acknowledgements. General Aspects.
Rate acceleration in enzyme-catalyzed reactions. Michaelis-Menten kinetics. Enzyme inhibition. Specificity. Improvement or alteration of enzyme specifity. Enzyme stabilization and reactor configuration. Cofactor regeneration. Enzyme catalysis in organic solvents. Multienzyme systems and metabolic engineering. Rational design of new enzymatic catalysts. Conclusion. References. Use of Hydrolytic Enzymes: Amidases, Proteases, Esterases, Lipases, Nitrilases, Phosphatases, Epoxide Hydrolases.
Amidases. Protease-catalyzed peptide synthesis. Proteases that act as esterases. Acetylcholine esterase. Pig liver esterase. Phospholipases. Cholesterol esterase. Lipases. Nitrile hydrolysis enzymes. Epoxide hydrolase. Phosphatase. References. Oxidoreductions.
Nicotinamide cofactor dependent oxidoreductions. Dehydrogenases which utilize ketoacids as substrates. Other NAD(P)-dependent dehydrogenases. Oxidoreductases that are metalloenzymes. References. C-C Bond Formation.
Aldol condensation. Ketol and aldol transfer reaction. Addition of HCN to aldehydes. Acyloin condensation. C-C bond forming reactions involving acetyl coA. Isoprenoid and steroid synthesis. &bgr;-replacement of chloroalanine. C-C bond formation catalyzed by vitamin B12
. References. Synthesis of Glycoside Bonds.
Background. Glycosyltransferases of the Leloir pathway. Substrate specificity and synthetic applications of glycosyltransferases. Non-Leloir glycosyltransferases. Glycosidases. Transglycosidases. Synthesis of N
-glycosides. Biological applications of synthetic glycoconjugates. Future opportunities. References. Addition, Elimination and Other Group Transfer Reactions (Phosphoryl-, Methyl-, Sulpho- and Amino-Transfer Reactions).
Addition of water to alkenes: fumarase. Addition of ammonia to double bonds: ammonia lyases. Transamination: aminotransferases. Addition and elimination of carboxyl group. Nucleoside triphosphate requiring enzymatic reactions. Preparation of ATP chiral at &agr;-, &bgr;- or &ggr;-phosphorous. Phosphorothioate-containing DNA and RNA. DNA and RNA oligomers. Incorporation of modified or unnatural bases into DNA or RNA. Dehalogenation. Synthesis of chiral methyl groups. S
-Adenosylmethionine and transmethylation. Sulfate activation and transfer reactions. References. Subject index.
Quotes and reviews
@from:Stanley M. Roberts
@qu:In summary this is an important text book written by two persons with outstanding reputations in the field. For a scientist working in the area it is like a good novel - having started to read it you cannot put it down. However, perhaps more importantly, it will serve as an excellent introduction for those persons wishing to get the flavour of the various techniques.
@qu:This unique and outstanding book presents a well-documented review of the use of enzymes in recognised areas of organic syntheses.... The wealth of detail is remarkable, and use of the subject index provides access to methods of bioconversion within each category covered by the five chapters. This book is highly recommended to organic chemists who wish to adopt biocatalysts to achieve synthetic specifications, and who require some background information in applied enzymology and enzyme biotechnology.
@source:Chemistry amp; Industry
@qu:Transformations based on enzymatic catalysis are providing an increasingly valuable component of the methodology of enantioselective synthesis. The advantages of using biocatalysts include relatively low cost, mild reaction conditions, and good yields of products with high enantiomeric excesses. In this book, 'Enzymes in Synthetic Organic Chemistry', Chi-Huey Wong and George Whitesides have succeeded in producing an extremely valuable reference text to this area of catalysis.... In this book, Wong and Whitesides have clearly described the value of biocatalysts to effect a broad range of organic transformations on a synthetically useful scale. In addition they have brought to the attention of the reader some of the potential problems to be considered in the use of enzymes in synthesis. I highly recommend this text not only as an excellent introduction to those who are making their first venture into the use of biocatalysts in their research but also as a valuable reference guide to experts in this field.
@source:Natural Product Reports
@from:Carl R. Johnson, Wayne State University
@qu:This book is thorough, up-to-date, highly readable, and very instructive for both novices and experienced practitioners in this rapidly growing area of chemistry. The authors, noted for their outstanding practical advances in the applications of enzymes in synthetic chemistry, have provided insight and encouraging commentary on harnessing the remarkable power of these natural catalysts in synthetic endeavors.... This book is by far the best effort to date for those interested in using enzymes in the context of organic syntheses. This economical paperback is recommended for personal and library collections and as a text for a special topics course.
@source:Journal American Chemical Society
@qu:The book of Wong and Whitesides represents an outstanding contribution to literature for Laboratories working on organic and bio-organic synthesis. This book belongs on every bio-organic chemist's bookshelf as well.
@source:Bulgarian Chemical Communications Vol 27, Number 1
@qu:Volume 12 In the Tetrahedron Organic Chemistry Series is, like its predeccessors, an excellent text providing both specialist and general information. As the use of enzymes in organic synthesis becomes more commonplace, this book by two widely acknowledged authorities in the area is a welcomed condensation of much of the literature to date... This book is thorough, well referenced well presented and as such is highly recommended to both libraries and individuals. It is an honest account of the strengths and limitations of enzymes in organic chemistry and strongly supports the notion that enzymes can be simply considered as alternative synthetic reagents, allowing expansion of the currently available amoury of the synthetic organic chemist.
@source:Chemistry in Australia