Biotechnology: Biotransformations I, Volume 8a, Second Edition

606 Pages·1998·16.749 MB·English

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.
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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