Biotechnology: Biotransformations I, Volume 8a, Second Edition PDF
Preview Biotechnology: Biotransformations I, Volume 8a, Second Edition
Biot echnology Second Edition Volume 8a Biotransfonnations I @ WILEY-VCH Biotechnology Second Edition Fundamentals Special Topics Volume 1 Volume 9 Biological Fundamentals Enzymes, Biomass, Food and Feed Volume 2 Volume 10 Genetic Fundamentals and Special Processes Genetic Engineering Volumes lla and b Volume 3 Environmental Processes Bioprocessing Volume 12 Volume 4 Legal, Economic and Measuring, Modelling, and Control Ethical Dimensions Products Volume 5 Recombinant Proteins, Monoclonal Antibodies and Therapeutic Genes Volume 6 Products of Primary Metabolism Volume 7 Products of Secondary Metabolism Volumes 8a and b Biotransformations I and I1 A Multi-Volume Comprehensive Treatise Biotechnology Second, Completely Revised Edition Edited by H.-J. Rehm and G. Reed in cooperation with A. Bhler and Stadler P. Volume 8a Bio ransformations I t Edited by D. R. Kelly CB WILEY-VCH Weinheim . New York . Chichester . Brisbane Singapore Toronto * Series Editors: Volume Editor: Prof. Dr. H.-J. Rehm Dr. G. Reed Dr. D. R. Kelly Institut fur Mikrobiologie 1029 N. Jackson St. #501-A Cardiff University of Wales Universitat Munster Milwaukee, WI 53202-3226 P.O. Box 912 CorrensstraBe 3 USA Cardiff, CF1 3TB, Wales D-48149 Munster UK FRG Prof. Dr. A. Puhler Prof. Dr. P. J. W. Stadler Biologie VI (Genetik) Artemis Pharmaceuticals Universitat Bielefeld Geschaftsfuhrung P.O. Box 100131 WilhelrnstraBe 10 D-33501 Bielefeld D-42755 Haan FRG FRG This book was carefully produced. Nevertheless, authors, editors and publisher do not warrant the information contained therein to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, procedural details or other items may inadvertently be inaccurate. Library of Congress Card No.: applied for British Library Cataloguing-in-Publication Data: A catalogue record for this book is available from the British Library Die Deutsche Bibliothek - CIP-Einheitsaufnahme Biotechnology : a multi volume comprehensive treatise I ed. by H.-J. Rehm and G. Reed. In cooperation with A. Piihler and P. Stadler. - 2., completely rev. ed. -VCH. ISBN 3-527-28310-2 (Weinheim ...) NE: Rehm, Hans-J. [Hrsg.] Vol. 8a: Biotransformations I I ed. by D. R. Kelly - 1998 ISBN 3-527-28318-8 OWILEY-VCH Verlag GmbH, D-69469 Weinheim (Federal Republic of Germany), 1998 Printed on acid-free and chlorine-free paper. All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form-by photoprinting, microfilm, or any other means-nor transmitted or translated into a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifi- cally marked as such, are not to be considered unprotected by law. Composition and Printing: Zechnersche Buchdruckerei, D-67330 Speyer. Bookbinding: J. Schaffer, D-67269 Griinstadt. Printed in the Federal Republic of Germany Preface In recognition of the enormous advances in series. Its members come from key institu- biotechnology in recent years, we are pleased tions representing scientific input from about to present this Second Edition of “Biotech- twenty countries. nology” relatively soon after the introduction The volume editors and the authors of the of the First Edition of this multi-volume com- individual chapters have been chosen for prehensive treatise. Since this series was ex- their recognized expertise and their contribu- tremely well accepted by the scientific com- tions to the various fields of biotechnology. munity, we have maintained the overall goal Their willingness to impart this knowledge to of creating a number of volumes, each de- their colleagues forms the basis of “Biotech- voted to a certain topic, which provide scien- nology” and is gratefully acknowledged. tists in academia, industry, and public institu- Moreover, this work could not have been tions with a well-balanced and comprehensive brought to fruition without the foresight and overview of this growing field. We have fully the constant and diligent support of the pub- revised the Second Edition and expanded it lisher. We are grateful to VCH for publishing from ten to twelve volumes in order to take “Biotechnology” with their customary excel- all recent developments into account. lence. Special thanks are due to Dr. Hans- These twelve volumes are organized into Joachim Kraus and Karin Dembowsky, with- three sections. The first four volumes consid- out whose constant efforts the series could er the fundamentals of biotechnology from not be published. Finally, the editors wish to biological, biochemical, molecular biological, thank the members of the Scientific Advisory and chemical engineering perspectives. The Board for their encouragement, their helpful next four volumes are devoted to products of suggestions, and their constructive criticism. industrial relevance. Special attention is given here to products derived from genetically en- H.-J. Rehm gineered microorganisms and mammalian G. Reed cells. The last four volumes are dedicated to A. Puhler the description of special topics. P. Stadler The new “Biotechnology” is a reference work, a comprehensive description of the state-of-the-art, and a guide to the original literature. It is specifically directed to micro- biologists, biochemists, molecular biologists, bioengineers, chemical engineers, and food and pharmaceutical chemists working in indus- try, at universities or at public institutions. A carefully selected and distinguished Scientific Advisory Board stands behind the Scientific Advisory Board Pro$ Dr. M. J. Beker Prof Dr. T. K. Ghose August Kirchenstein Institute of Microbiology Biochemical Engineering Research Centre Latvian Academy of Sciences Indian Institute of Technology Riga, Latvia New Delhi, India Prof Dr. J. D. Bu’Lock Prof Dr. I. Goldberg Weizmann Microbial Chemistry Laboratory Department of Applied Microbiology Department of Chemistry The Hebrew University University of Manchester Jerusalem, Israel Manchester, UK Prof Dr. C. L. Cooney Prof: Dr. G. Goma Department of Chemical Engineering Departement de Genie Biochimique et Massachusetts Institute of Technology Alimentaire Cambridge, MA, USA Institut National des Sciences Appliquees Toulouse, France Prof Dr. H. W. Doelle Sir D. A. Hopwood Department of Microbiology Department of Genetics University of Queensland John Innes Institute St. Lucia, Australia Norwich, UK Prof Dr. J. Drews Prof Dr. E. H. Houwink F. Hoffmann-La Roche AG Organon International bv Basel, Switzerland Scientific Development Group Oss. The Netherlands Prof Dr. A. Fiechter Prof Dr. A. E. Humphrey Institut fur Biotechnologie Center for Molecular Bioscience and Eidgenossische Technische Hochschule Biotechnology Zurich, Switzerland Lehigh University Bethlehem, PA, USA VIII Scientific Advisory Board Prof Dr. I. Karube Prof Dr. K. Schiigerl Research Center for Advanced Science Institut fur Technische Chemie and Technology Universitat Hannover University of Tokyo Hannover, Germany Tokyo, Japan Prof Dr. M. A. Lachance Prof Dr. P. Sensi Department of Plant Sciences Chair of Fermentation Chemistry University of Western Ontario and Industrial Microbiology London, Ontario, Canada Lepetit Research Center Gerenzano, Italy Prof Dr. Y. Liu Prof Dr. Y. H. Tan China National Center for Biotechnology Institute of Molecular and Cell Biology Development National University of Singapore Beijing, China Singapore Prof Dr. J. F. Martin Prof Dr. D. Thomas Department of Microbiology Laboratoire de Technologie Enzymatique University of Leon Universite de Compiegne Leon, Spain Compiegne, France ProJ Dr. B. Mattiasson Prof Dr. W. Verstraete Department of Biotechnology Laboratory of Microbial Ecology Chemical Center Rijksuniversiteit Gent University of Lund Gent, Belgium Lund. Sweden Prof Dr. M. Roehr Prof Dr. E.- L. Winnacker Institut fur Biochemische Technologie Institut fur Biochemie und Mikrobiologie Universitat Miinchen Technische Universitat Wien Munchen, Germany Wien. Austria Prof Dr. H. Sahm Institut fur Biotechnologie Forschungszentrum Julich Jiilich, Germany Contents Introduction 1 Redox Enzymes D. R. Kelly 7 Alkaloids 327 1 Perspectives in Biotransformation 5 N Bruce M.T urner 8 Yeast 363 2 Biotransformations - Practical Aspects 25 S. Servi D. R. Kelly 9 Alcohol Dehydrogenases - Characteristics, Design of Reaction Conditions, and Applications 391 J. Peters Hydrolases 10 Hydroxylation and Dihydroxylation 475 H. Holland 11 Flavin Monooxygenases- Uses as Catalysts 3 Biotransformations with Lipases 37 for Baeyer-Villiger Ring Expansion R. Katlauskas, U. Bornscheuer and Heteroatom Oxidation 535 4 Esterases 193 D. R. Kelly, f? Wan,J . Tsang Phvthian S. 5 C1ea;age and Formation Index 589 of Amide Bonds 243 D. Hoople 6 Nitriles 277 A. Bunch Contributors Dr. Uwe Bornscheuer Dr. David Hoople Universitat Stuttgart Pfizer Central Research Allmandring 31 Ramsgate Rd. D-70569 Stuttgart Sandwich, Kent, CT13 9NJ Germany UK Chapter 3 Chapter 5 Dr. Neil Bruce Prof. Romas J. Kazlauskas Institute of Biotechnology Department of Chemistry University of Cambridge McGill University Cambridge, CB2 1QT 801 Sherbrooke St. W. UK MontrCal, Quebec H3A 2K6 Chapter 7 Canada Chapter 3 Dr. Alan Bunch Dr. David R. Kelly Biological Laboratory Cardiff University of Wales University of Kent PO. Box 912 Canterbury, Kent Cardiff, CFl 3TB UK UK Chapter 6 Chapters 2 and I I Prof. Herbert L. Holland Dr. Jorg Peters Department of Chemistry Bayer AG Brock University Geschaftsbereich Pharma St. Catharines, Ontario, L2S 3A1 TO Biotechnologie Canada D-42096 Wuppertal Chapter I0 Germany Chapter 9 XI1 Contributors Dr. Sara Phythian Prof. Michael K. Turner Natural Resources Institute The Advanced Center The University of Greenwich for Biochemical Engineering Central Avenue, Chatham Maritime Department of Chemical Kent ME4 and Biochemical Engineering 4TB UK University College London Chapter 4 Torrington Place London, WClE 7JE UK Chapter 1 Prof. Stefan0 Servi Dr. Peter W. H. Wan Dipartimento Chimico Department of Chemistry Politech Milan Imperial College of Science, Technology Via Marcinelli 7 and Medicine 1-20131 Milano Exhibition Road, South Kensington Italy London, SW7 2AY Chapter 8 UK Chapter I1 Dr. Jenny Tsang Department of Chemistry The Robert Robinson Laboratories University of Liverpool PO. Box 147 Liverpool, L69 3BX UK Chapter I1
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