Practical Methods for Biocatalysis and Biotransformations · 2016-08-12 · Practical Methods for...

Practical Methods forBiocatalysis and

Biotransformations

Editors

JOHN WHITTALL

Manchester Interdisciplinary Biocentre,University of Manchester, United Kingdom

PETER SUTTON

Synthetic Chemistry, GlaxoSmithKline R&D Ltd,United Kingdom

A John Wiley and Sons, Ltd., Publication

Practical Methods for Biocatalysis and

Biotransformations

Practical Methods forBiocatalysis and

Biotransformations

Editors

JOHN WHITTALL

Manchester Interdisciplinary Biocentre,University of Manchester, United Kingdom

PETER SUTTON

Synthetic Chemistry, GlaxoSmithKline R&D Ltd,United Kingdom

A John Wiley and Sons, Ltd., Publication

This edition first published 2010

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Library of Congress Cataloging-in-Publication Data

Practical methods for biocatalysis and biotransformations / editors,

John Whittall, Peter Sutton.

p. ; cm.

Includes bibliographical references and index.

ISBN 978-0-470-51927-1

1. Enzymes—Biotechnology. 2. Biotransformation (Metabolism) 3. Organic compounds—

Synthesis. I. Whittall, John. II. Sutton, Peter (Peter W.)

[DNLM: 1. Biocatalysis. 2. Biotransformation. 3. Enzymes. QU 135 P895 2009]

TP248.65.E59P73 2009

660.6034—dc22

2009030811

A catalogue record for this book is available from the British Library.

ISBN 978-0-470-51927-1

Set in 10/12pt Times by Integra Software Services Pvt. Ltd, Pondicherry, India

Printed and bound in Great Britain by CPI Antony Rowe, Chippenham, Wiltshire

www.wiley.com

Contents

Preface xi

Abbreviations xiii

List of Contributors xix

1 Biotransformations in Small-molecule Pharmaceutical Development 1

Joseph P. Adams, Andrew J. Collis, Richard K. Henderson and Peter

W. Sutton

2 Biocatalyst Identification and Scale-up: Molecular Biology for

Chemists 83

Kathleen H. McClean

3 Kinetic Resolutions Using Biotransformations 117

3.1 Stereo- and Enantio-selective Hydrolysis of rac-2-Octylsulfate Using

Whole Resting Cells of Pseudomonas spp. 117

Petra Gadler and Kurt Faber

3.2 Protease-catalyzed Resolutions Using the 3-(3-Pyridine)propionyl

Anchor Group: p-Toluenesulfonamide 121

Christopher K. Savile and Romas J. Kazlauskas

3.3 Desymmetrization of Prochiral Ketones Using Enzymes 125

Andrew J. Carnell

3.4 Enzymatic Resolution of 1-Methyl-tetrahydroisoquinoline

using Candida rugosa Lipase 129

Gary Breen

4 Dynamic Kinetic Resolution for the Synthesis of Esters, Amides and

Acids Using Lipases 133

4.1 Dynamic Kinetic Resolution of 1-Phenylethanol by Immobilized

Lipase Coupled with In Situ Racemization over Zeolite Beta 133

Kam Loon Fow, Yongzhong Zhu, Gaik Khuan Chuah and Stephan

Jaenicke

4.2 Synthesis of the (R)-Butyrate Esters of Secondary Alcohols by

Dynamic Kinetic Resolution Employing a Bis(tetrafluorosuccinato)-

bridged Ru(II) Complex 137

S.F.G.M. van Nispen, J. van Buijtenen, J.A.J.M. Vekemans,

J. Meuldijk and L.A. Hulshof

4.3 Dynamic Kinetic Resolution 6,7-Dimethoxy-1-methyl-1,2,3,4-

tetrahydroisoquinoline 141

Michael Page, John Blacker and Matthew Stirling

4.4 Dynamic Kinetic Resolution of Primary Amines with a Recyclable

Palladium Nanocatalyst (Pd/AlO(OH)) for Racemization 148

Soo-Byung Ko, Mahn-Joo Kim and Jaiwook Park

4.5 Dynamic Kinetic Resolution of Amines Involving Biocatalysis and

In Situ Free-radical-mediated Racemization 153

Stephane Gastaldi, Gerard Gil and Michele P. Bertrand

4.6 Chemoenzymatic Dynamic Kinetic Resolution of (S)-Ibuprofen 157

A.H. Kamaruddin and F. Hamzah

4.7 Dynamic Kinetic Resolution Synthesis of a Fluorinated Amino Acid

Ester Amide by a Continuous Process Lipase-mediated Ethanolysis

of an Azalactone 162

Matthew Truppo, David Pollard, Jeffrey Moore and Paul Devine

5 Enzymatic Selectivity in Synthetic Methods 165

5.1 Alcalase-catalysed Syntheses of Hydrophilic Di- and Tri-peptides in

Organic Solvents 165

Xue-Zhong Zhang, Rui-Zhen Hou, Li Xu and Yi-Bing Huang

5.2 Selective Alkoxycarbonylation of 1�,25-Dihydroxyvitamin D3 Diol

Precursor with Candida antarctica Lipase B 170

Miguel Ferrero, Susana Fernandez and Vicente Gotor

5.3 The Use of Lipase Enzymes for the Synthesis of Polymers and

Polymer Intermediates 173

Alan Taylor

5.4 Bioconversion of 3-Cyanopyridine into Nicotinic Acid with Gordona

terrae NDB1165 182

Tek Chand Bhalla

5.5 Enzyme-promoted Desymmetrization of Prochiral Dinitriles 186

Marloes A. Wijdeven, Piotr Kiełbasinski and Floris P.J.T. Rutjes

5.6 Epoxide Hydrolase-catalyzed Synthesis of (R)-3-Benzyloxy-2-

methylpropane-1,2-diol 190

Takeshi Sugai, Aya Fujino, Hitomi Yamaguchi and Masaya Ikunaka

5.7 One-pot Biocatalytic Synthesis of Methyl (S)-4-Chloro-3-

hydroxybutanoate and Methyl (S)-4-Cyano-3-hydroxybutanoate 199

Maja Majeric Elenkov, Lixia Tang, Bernhard Hauer and Dick

B. Janssen

vi Contents

6 Aldolase Enzymes for Complex Synthesis 203

6.1 One-step Synthesis of L-Fructose Using Rhamnulose-1-phosphate

Aldolase in Borate Buffer 203

William A. Greenberg and Chi-Huey Wong

6.2 Straightforward Fructose-1,6-bisphosphate Aldolase-mediated

Synthesis of Aminocyclitols 206

Marielle Lemaire and Lahssen El Blidi

6.3 Synthesis of D-Fagomine by Aldol Addition of Dihydroxyacetone to

N-Cbz-3-AminopropanalCatalysedbyD-Fructose-6-phosphateAldolase 212

Jose A. Castillo, Teodor Parella, Tomoyuki Inoue, Georg

A. Sprenger, Jesus Joglar and Pere Clapes

6.4 Chemoenzymatic Synthesis of 5-Thio-D-xylopyranose 218

Franck Charmantray, Philippe Dellis, Virgil Helaine, Soth Samreth

and Laurence Hecquet

7 Enzymatic Synthesis of Glycosides and Glucuronides 227

7.1 Glycosynthase-assisted Oligosaccharide Synthesis 227

Adrian Scaffidi and Robert V. Stick

7.2 Glycosyl Azides: Novel Substrates for Enzymatic

Transglycosylations 232

Vladimır Kren and Pavla Bojarova

7.3 Facile Synthesis of Alkyl �-D-Glucopyranosides from D-Glucose and

the Corresponding Alcohols Using Fruit Seed Meals 236

Wen-Ya Lu, Guo-Qiang Lin, Hui-Lei Yu, Ai-Ming Tong and

Jian-He Xu

7.4 Laccase-mediated Oxidation of Natural Glycosides 240

Cosimo Chirivı, Francesca Sagui and Sergio Riva

7.5 Biocatalysed Synthesis of Monoglucuronides of Hydroxytyrosol,

Tyrosol, Homovanillic Alcohol and 3-(40-Hydroxyphenyl)propanol

Using Liver Cell Microsomal Fractions 245

Olha Khymenets, Pere Clapes, Teodor Parella, Marıa-Isabel Covas,

Rafael de la Torre, and Jesus Joglar

7.6 Synthesis of the Acyl Glucuronide of Mycophenolic Acid 251

Matthias Kittelmann, Lukas Oberer, Reiner Aichholz and Oreste

Ghisalba

8 Synthesis of Cyanohydrins Using Hydroxynitrile Lyases 255

8.1 Synthesis of (S)-2-Hydroxy-2-methylbutyric Acid by a

Chemoenzymatic Methodology 255

Manuela Avi and Herfried Griengl

8.2 (S)-Selective Cyanohydrin Formation from Aromatic Ketones Using

Hydroxynitrile Lyases 259

Chris Roberge, Fred Fleitz and Paul Devine

Contents vii

8.3 Hydroxynitrile-lyase-catalysed Synthesis of Enantiopure

(S)-Acetophenone Cyanohydrins 262

Jan von Langermann, Annett Mell, Eckhard Paetzold and Udo Kragl

8.4 (R)- and (S)-Cyanohydrin Formation from Pyridine-

3-carboxaldehyde Using CLEATM-immobilized Hydroxynitrile Lyases 266

Chris Roberge, Fred Fleitz and Paul Devine

8.5 A New (R)-Hydroxynitrile Lyase from Prunus mume for Asymmetric

Synthesis of Cyanohydrins 269

Yasuhisa Asano

9 Synthesis of Chiral sec-Alcohols by Ketone Reduction 273

9.1 Asymmetric Synthesis of (S)-Bis(trifluoromethyl)phenylethanol by

Biocatalytic Reduction of Bis(trifluoromethyl)acetophenone 273

David Pollard, Matthew Truppo and Jeffrey Moore

9.2 Enantioselective and Diastereoselective Enzyme-catalyzed Dynamic

Kinetic Resolution of an Unsaturated Ketone 276

Birgit Kosjek, David Tellers and Jeffrey Moore

9.3 Enzyme-catalysed Synthesis of �-Alkyl-�-hydroxy Ketones and

Esters by Isolated Ketoreductases 278

Ioulia Smonou and Dimitris Kalaitzakis

9.4 Asymmetric Reduction of Phenyl Ring-containing Ketones Using

Xerogel-encapsulated W110A Secondary Alcohol Dehydrogenase

from Thermoanaerobacter ethanolicus 284

Musa M. Musa, Karla I. Ziegelmann-Fjeld, Claire Vieille, J. Gregory

Zeikus and Robert S. Phillips

9.5 (R)- and (S)-Enantioselective Diaryl Methanol Synthesis Using

Enzymatic Reduction of Diaryl Ketones 288

Matthew Truppo, Krista Morley, David Pollard and Paul Devine

9.6 Highly Enantioselective and Efficient Synthesis of

Methyl (R)-o-Chloromandelate, Key Intermediate for Clopidogrel

Synthesis, with Recombinant Escherichia coli 291

Tadashi Ema, Nobuyasu Okita, Sayaka Ide and Takashi Sakai

10 Reduction of Functional Groups 295

10.1 Reduction of Carboxylic Acids by Carboxylic Acid Reductase

Heterologously Expressed in Escherichia coli 295

Andrew S. Lamm, Arshdeep Khare and John P.N. Rosazza

10.2 Light-driven Stereoselective Biocatalytic Oxidations and Reductions 299

Andreas Taglieber, Frank Schulz, Frank Hollmann, Monika Rusek

and Manfred T. Reetz

10.3 Unnatural Amino Acids by Enzymatic Transamination: Synthesis of

Glutamic Acid Analogues with Aspartate Aminotransferase 306

Thierry Gefflaut, Emmanuelle Sagot and Jean Bolte

viii Contents

10.4 Synthesis of L-Pipecolic Acid with �1-Piperidine-2-carboxylate

Reductase from Pseudomonas putida 310

Hisaaki Mihara and Nobuyoshi Esaki

10.5 Synthesis of Substituted Derivatives of L-Phenylalanine and of other

Non-natural L-Amino Acids Using Engineered Mutants of

Phenylalanine Dehydrogenase 314

Philip Conway, Francesca Paradisi and Paul Engel

11 Enzymatic Oxidation Chemistry 319

11.1 Monoamine Oxidase-catalysed Reactions: Application Towards the

Chemo-enzymatic Deracemization of the Alkaloid (–)-Crispine A 319

Andrew J. Ellis, Renate Reiss, Timothy J. Snape and Nicholas

J. Turner

11.2 Glucose Oxidase-catalysed Synthesis of Aldonic Acids 323

Fabio Pezzotti, Helene Therisod and Michel Therisod

11.3 Oxidation and Halo-hydroxylation of Monoterpenes with

Chloroperoxidase from Leptoxyphium fumago 327

Bjoern-Arne Kaup, Umberto Piantini, Matthias Wust and Jens

Schrader

11.4 Chloroperoxidase-catalyzed Oxidation of Phenyl Methylsulfide in

Ionic Liquids 330

Cinzia Chiappe

11.5 Stereoselective Synthesis of �-Hydroxy Sulfoxides Catalyzed by

Cyclohexanone Monooxygenase 332

Stefano Colonna, Nicoletta Gaggero, Sara Pellegrino and Francesca

Zambianchi

11.6 Enantioselective Kinetic Resolution of Racemic 3-Phenylbutan-2-

one Using a Baeyer–Villiger Monooxygenase 337

Anett Kirschner and Uwe T. Bornscheuer

11.7 Desymmetrization of 1-Methylbicyclo[3.3.0]octane-2,8-dione by the

Retro-claisenase 6-Oxo Camphor Hydrolase 341

Gideon Grogan and Cheryl Hill

11.8 Synthesis of Optically Pure Chiral Lactones by Cyclopentadecanone

Monooxygenase-catalyzed Baeyer–Villiger Oxidations 344

Shaozhao Wang, Jianzhong Yang and Peter C.K. Lau

12 Whole-cell Oxidations and Dehalogenations 351

12.1 Biotransformations of Naphthalene to 4-Hydroxy-1-tetralone by

Streptomyces griseus NRRL 8090 351

Arshdeep Khare, Andrew S. Lamm and John P.N. Rosazza

12.2 Hydroxylation of Imidacloprid for the Synthesis of Olefin

Imidacloprid by Stenotrophomonas maltophilia CGMCC 1.1788 355

Sheng Yuan and Yi-jun Dai

Contents ix

12.3 Biocatalytic Synthesis of 6-Hydroxy Fluvastatin using Motierella

rammaniana DSM 62752 in Shake Flask Culture and on Multi-gram

Scale using a Wave Bioreactor 359

Matthias Kittelmann, Maria Serrano Correia, Anton Kuhn, Serge

Parel, Jurgen Kuhnol, Reiner Aichholz, Monique Ponelle and Oreste

Ghisalba

12.4 Synthesis of 1-Adamantanol from Adamantane through

Regioselective Hydroxylation by Streptomyces griseoplanus Cells 367

Koichi Mitsukura, Yoshinori Kondo, Toyokazu Yoshida and Toru

Nagasawa

12.5 Enantioselective Benzylic Microbial Hydroxylation of Indan and

Tetralin 369

Renata P. Limberger, Cleber V. Ursini, Paulo J.S. Moran and

J. Augusto R. Rodrigues

12.6 Stereospecific Biotransformation of (R,S)-Linalool by Corynespora

cassiicola DSM 62475 into Linalool Oxides 376

Marco-Antonio Mirata and Jens Schrader

12.7 The Biocatalytic Synthesis of 4-Fluorocatechol from Fluorobenzene 379

Louise C. Nolan and Kevin E. O’Connor

12.8 Synthesis of Enantiopure (S)-Styrene Oxide by Selective Oxidation

of Styrene by Recombinant Escherichia coli JM101 (pSPZ10) 385

Katja Buehler and Andreas Schmid

12.9 Biotransformation of �-Bromo and �,�0-Dibromo Alkanone into

�-Hydroxyketone and �-Diketone by Spirulina platensis 391

Takamitsu Utsukihara and C. Akira Horiuchi

Index 397

x Contents

Preface

During the early to mid 1990s Professor Stan Roberts was chief editor of a series of loose-

leaf laboratory protocols detailing the use of biotransformations in synthetic organic

chemistry that were collected together and published in book form (Preparative

Biotransformations, Wiley, Chichester, 1999). This led to the publication of the series of

books Catalysts for Fine Chemical Synthesis, volumes 1–5, by the same publisher which

covered the application of chemo- and bio-catalytic procedures for the synthesis of fine

chemicals; for this series, Dr John Whittall became co-editor on the homogeneous cata-

lysis volumes. Following the format of this series, Practical Methods in Biocatalysis and

Biotransformations has been prepared. In keeping with these earlier formats, we aim to

provide the readership with enough information to understand when a biocatalytic or

biotransformation method would be a suitable practical method to carry out their synthetic

transformation.

In recent times, the employment of enzymes and whole cells to perform a range of

organic reactions has become much more commonplace, and biotransformation has

become accepted as a powerful method for application in synthetic organic chemistry.

However, for chemists developing synthetic methods for a particular target molecule, the

understanding of the advantages and limitations of biocatalysis and biotransformation is

not always clear. Therefore, this book intends to review the industrial background to when

biotransformations are used and introduce the nonmicrobiologist to the background of how

biocatalysts are discovered and developed and then give detailed experimental procedures

for a comprehensive range of useful biotransformation methods.

In order to place the later chapters in proper context, Chapter 1 offers a comprehensive

review of biotransformation from the perspective of a large pharmaceutical company

(GSK) and Chapter 2 gives an introduction that allows an appreciation of molecular

biology for scientists with no formal training in this area.

In the remaining chapters, key biotransformations have been identified from the recent

primary literature (learned journals) and the respective authors have amplified the dis-

closure of their methodologies in this volume. These disclosures often contain additional

equipment and experimental details to those found in the experimental section of most

journals, allowing the reader to decide whether these methods are suitable for addressing

their needs.

Chapter 3 describes the application of lipases, proteases and sulfatases for the kinetic

resolution of a range of interesting molecules. A selection of dynamic kinetic resolution

(DKR) procedures is disclosed in Chapter 4. DKRs are attracting a significant amount of

interest as they allow access to >50 % yields of single enantiopure products from

racemates. Other useful synthetic applications of hydrolase enzymes are covered in

Chapter 5, including desymmetrization and regio- and chemo-selective transformations.

Chapters 6 and 7 cover sugar-type chemistry, focusing on aldol and glycosylation

methods which can offer substantial advantages over traditional chemical approaches.

Chapter 8 describes the application of hydroxyl nitrile lyases to the synthesis of new

chiral cyanohydrins and �-hydroxy acids and includes new approaches to the transforma-

tion of ‘difficult’ aldehyde and ketone substrates using substrate engineering and immo-

bilization techniques.

The latter part of the book is dedicated to redox biotransformation application, with

Chapter 9 disclosing several methods for the synthesis of chiral secondary alcohols using a

range of commercially available ketoreductases (alcohol dehydrogenases) which are now

being applied regularly on a large scale.

Chapter 10 covers reductive enzymes with an emphasis on transaminase enzymes,

which are enjoying widespread application in the synthesis of nonnatural amino acids

which are key building blocks for several products of industrial importance.

The use of a range of oxidative enzymes in synthesis is covered in Chapter 11, whilst the

very powerful technique of regio- and stereo-specific biohydroxylation of even complex

molecules by fermenting whole-cell methods is covered in Chapter 12.

The Editors are most grateful to the authors who have submitted details of their

procedures in the prescribed format for inclusion in this book. We hope that this book

will increase the exposure of these methods to the chemical community and contribute to

the expanded employment of biocatalysis in organic synthesis.

John Whittall, Manchester

Peter Sutton, Stevenage

2009

xii Preface

Abbreviations

A adenine

ABTS 2,20-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid

7-ACA 7-aminocephalosporanic acid

ACN acetonitrile

AcOH acetic acid

ACS GCI American Chemical Society Green Chemistry Institute

7-ADCA 7-aminodesacetoxycephalosporanic acid

ADH alcohol dehydrogenase (alternative name for a ketoreductases or KREDs)

ADH-RE alcohol dehydrogenase from Rhodococcus erythropolis

AIBN 2,20-azobis(2-methylpropionitrile)

6-APA 6-aminopenicillanic acid

API active pharmaceutical ingredient

Ara-G 9-b-D-arabinofuranosylguanidine

Ara-U 9-b-D-arabinofuranosyluridine

AspAT aspartate aminotransferase

AT aminotransferases

AZT 30-azido-20,30-dideoxythymidine (zidovudine)

BEHP bis(2-ethylhexyl)phthalate

BES N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid

BLAST basic local alignment search tool

BREP butanol-rinsed enzyme preparation

BSA bovine serum albumin

BSA N-bromosuccinimide

BVMO Baeyer–Villiger monooxygenase

C cytosine

CAL-A lipase A from Candida antarctica

CAL-B lipase B from Candida antarctica

Car carboxylic acid reductase

CASTing combinatorial active site saturation test

Cbz Benzyloxycarbonyl

CCL lipase from Candida cylindracea (now known as lipase from

Candida rugosa or CRL)

CDI 1,10-carbonyldiimidazole

CDW cell dry weight

cGMP current good manufacturing practice

CHMO cyclohexanone monooxygenase

CINV chemotherapy-induced nausea

CLEA cross-linked enzyme aggregate

CLEC cross-linked enzyme crystal

CNS Central nervous system

CPDMO cyclopentadecanone monooxygenase

CPO chloroperoxidase

CRL lipase from Candida rugosa

CSA cysteine sulfinic acid

CYP cytochrome P450

DBDMH N,N0-dibromodimethylhydantoin

DBE di-n-butylether

DCM dichloromethane

DCW dry cell weight

DDI drug–drug interaction

DERA 2-deoxyribose-5-phosphate aldolase

dGTP deoxyguanosine triphosphate

DHA dihydroxyacetone

DHAP dihydroxyacetone phosphate

DHF dihydrofolate

DIPE diisopropylether

DKR dynamic kinetic resolution

DMAP 4-dimethylaminopyridine

DMF dimethylformamide

DMSO dimethylsulfoxide

DNA deoxyribonucleic acid

DNAse deoxyribonuclease

dNTP deoxyribonucleotide triphosphate

DoE design of experiment

DOT dissolved oxygen tension

DSMZ Deutsche Sammlung von Mikroorganismen und Zellkulturen

dsDNA double-stranded DNA

D4T dideoxydidehydrothymidine

DTT dithiothreitol

dUDP 20-deoxyuridine-50-diphosphate

dUMP 20-deoxyuridine-50-monophosphate

E enantiomeric ratio

EDC 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

EDTA ethylenediaminetetraacetic acid

xiv Abbreviations

EHS environmental health and safety

epPCR error-prone PCR

EtOAc Ethyl acetate

FACS fluorescence-activated cell sorting

FAD flavin adenine dinucleotide

FADH2 flavin adenine dinucleotide, reduced form

FASTA FAST ALL (a programme for fast protein comparison or fast

nucleotide sequence comparison)

FDA Food and Drug Administration (United States)

FDH formate dehydrogenase

FMN flavin mononucleotide (riboflavin-50-phosphate)

FPLC fast protein liquid chromatography

FruA fructose-1,6-bisphosphate aldolase

FSA D-fructose-6-phosphate aldolase

FTIR Fourier-transform infrared spectroscopy

GABA g-aminobutyric acid

G guanine

GC gas chromatography

GDH glucose dehydrogenase

GlcI glucose isomerase

GMO genetically modified organism

GMM genetically modified microorganism

G6P glucose-6-phosphate

G6PDH glucose-6-phosphate dehydrogenase

GPC gel permeation chromatography

GPO L-glycerol-3-phosphate oxidase

GR glucocorticoid receptor

GRAS generally recognized as safe

GSK GlaxoSmithKline

HBV hepatitis B virus

HEPES 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid

HIV human immunodeficiency virus

HMQC heteronuclear multiple quantum coherence

HNL hydroxynitrile lyase

HOBt 1-hydroxybenzotriazole

HOPhPr hydroxyphenylpropanol

HOTYR hydroxytyrosol

HPA hydroxypyruvate

HPI N-hydroxyphthalimide

HPLC high-performance liquid chromatography

HTS high-throughput screening

HVAlc Homovanillic alcohol

Abbreviations xv

IMI imidacloprid

Indels insertions and deletions

IP intellectual property

IPTG isopropyl-b-D-thiogalactopyranoside

ISPR in situ product removal

KPB potassium phosphate buffer

KR kinetic resolution

KRED ketoreductase (alternative name for an alcohol dehydrogenase or ADH)

LAS lovastatin ammonium salt

LB Luria–Bertani

LCA life cycle analysis

LovD acyltransferase from the lovastatin biosynthetic pathway

Mab monoclonal antibody

MAO-N monoamine oxidase

MEA malt extract agar

MES 2-morpholino ethansulfonic acid monohydrate

MGF minimum genome factories

MML lipase from Mucor sp.

MOPS 3-morpholino propane sulfonic acid

m.p. melting point

MPA mycophenolic acid

MPLC medium-pressure chromatography

mRNA messenger RNA

MS molecular sieves

MTBE tert-butylmethylether

MTQ methyl-tetrahydroisoquinoline

MYB malt yeast broth

NADþ b-nicotinamide adenine dinucleotide

NADH b-nicotinamide adenine dinucleotide, reduced form

NADPH b-nicotinamide adenine dinucleotide 20-phosphate, reduced form

NADPþ b-nicotinamide adenine dinucleotide 20-phosphate

NAG N-acetyl-D-glucosamine

NAM N-acetyl-D-mannosamine

NANA N-acetyl-D-neuraminic acid

NCE new chemical entity

NK-1 neurokinin-1

NME new molecular entity

NMR nuclear magnetic resonance

NP nucleoside phosphorylase

OCH 6-oxo camphor hydrolase

ORI origin of replication

P450 cytochrome P450

xvi Abbreviations

P450 BM-3 cytochrome P450 BM-3 from Bacillus megaterium

PAMO phenylacetone monooxygenase

Pase acid phosphatase

PAT process analytical technology

PCL lipase from Pseudomonas cepacia (now renamed to Burkholderia

cepacia)

PCR polymerase chain reaction

PDCB potato–dextrose–carrot broth

PEP phosphoenolpyruvic acid

PFL lipase from Pseudomonas fluorescens

PGA penicillin G acylase

Pip2C D1-piperideine-2-carboxylate reductase

PLE pig liver esterase

pNPG p-nitrophenyl-b-D-glucopyranoside

PNP purine nucleoside phosphorylase

PPL porcine pancreatic lipase

ProSAR protein sequence–activity relationship

QbD quality by design

QSAR quantitative structure–activity relationship

RAMA rabbit muscle aldolase (fructose-1,6-bis-phosphate aldolase)

R&D research and development

rDNA recombinant DNA

rRNA ribosomal RNA

Rf retention factor

RhaD rhamnulose-1-phosphate aldolase

RNA ribonucleic acid

ROH generic alcohol

Rt retention time

SAS simvastatin ammonium salt

SCR Saccharomyces cerevisiae carbonyl reductase

SIGEX substrate-induced gene-expression screening

SMB simulated moving bed chromatography

SOT Spirulina–Ogawa–Terui

ssDNA single-stranded DNA

T thymine

Taq a thermostable DNA polymerase from Thermus aquaticus

TBDMSCl tert-butyldimethylsilyl chloride

TBME tert-butylmethylether

TCA trichloroacetic acid

TDP thymidine 50-phosphate

TdR thymidine

TEMPO 2,2,6,6-tetramethyl-1-piperidinyloxy

Abbreviations xvii

TFA trifluoroacetic acid

THF tetrahydrofuran

THFo tetrahydrofolate

ThDP thiamine pyrophosphate

TK transketolase

TLC thin-layer chromatography

TMP thymidine 50-monophosphate

TMS tetramethyl silane

TMOS tetramethyl orthosilicate

TMSOTf trimethylsilyl triflate

TP thymidine-50-phosphorylase

tris-HCl tris(hydroxymethyl)aminomethane HCl

TTN total turnover number

TYR tyrosol

U unit of enzyme activity (mmol min�1)

U uracil

UdR 20-deoxyuridine

UDP uridine-50-diphosphate

UTP uridine-50-triphosphate

UDPGA uridine-50-diphosphoglucuronic acid

UDPGT uridine-50-diphosphoglucuronyl transferase

URDP uridine-50-phosphorylase

UV ultraviolet

VVM gas volume flow per unit of liquid volume per minute

WFCC World Federation for Culture Collections

YPG yeast extract–peptone–glucose

xviii Abbreviations

List of Contributors

Joseph P. Adams, GlaxoSmithKline, Synthetic Chemistry, Gunnels Wood Road,

Stevenage, Hertfordshire SG1 2NY, UK

Reiner Aichholz, Metabolism and Pharmacokinetics, NIBR, Novartis Pharma AG,

CH-4002 Basel, Switzerland

Yasuhisa Asano, Biotechnology Research Center and Department of Biotechnology,

Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan

Manuela Avi, Institute of Organic Chemistry, Graz University of Technology,

Stremayrgasse 16, 8010 Graz, Austria

Michele P. Bertrand, Laboratoire de Chimie Moleculaire Organique, LCP UMR 6264,

Boite 562, Universite Paul Cezanne, Aix-Marseille III, Faculte des Sciences St Jerome,

Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France

Tek Chand Bhalla, Department of Biotechnology, Himachal Pradesh University, Shimla

171005, India

John Blacker, NPIL Pharma Ltd, Leeds Road, Huddersfield, HD1 9GA, UK

Lahssen El Blidi, Laboratoire SEESIB, UMR 6504 CNRS, Universite Blaise Pascal,

24 avenue des Landais 63177 Aubiere cedex, France

Pavla Bojarova, Institute of Microbiology, Center of Biocatalysis and

Biotransformations, Academy of Sciences of the Czech Republic, Vıdenska 1083,

CZ-142 20 Prague 4, Czech Republic

Jean Bolte, Department of Chemistry, Universite Blaise Pascal, Clermont-Ferrand, France

Uwe T. Bornscheuer, Department of Biotechnology and Enzyme Catalysis, Institute of

Biochemistry, Greifswald University, Felix-Hausdorff-Str. 4, 17487 Greifswald,

Germany

Gary Breen, GlaxoSmithKline, Synthetic Chemistry, Leigh, Tonbridge, Kent, TN11

9AN, UK

Katja Buehler, Laboratory of Chemical Biotechnology, Faculty of Biochemical and

Chemical Engineering, TU Dortmund, Emil-Figge-Strasse 66, 44221 Dortmund,

Germany

J. van Buijtenen, Eindhoven University of Technology, Laboratory of Macromolecular

and Organic Chemistry, PO Box 513, 5600 MB Eindhoven, The Netherlands

Andrew J. Carnell, Department of Chemistry, Robert Robinson Laboratories, University

of Liverpool, Liverpool, L69 7ZD, UK

Jose A. Castillo, Biotransformation and Bioactive Molecules Group, Instituto de Quimica

Avanzada de Cataluna, Consejo Superior de Investigaciones Cientificas, Jordi Girona

18-26, 08034 Barcelona, Spain

Franck Charmantray, Laboratoire SEESIB, UMR 6504 CNRS, Universite Blaise Pascal,

24 avenue des Landais, 63177 Aubiere, France

Cinzia Chiappe, Dipartimento di Chimica e Chimica Industriale, Universit di Pisa, 56126

Pisa, Italy

Cosimo Chirivı, Istituto di Chimica del Riconoscimento Molecolare, C.N.R., Via Mario

Bianco 9, 20131 Milano, Italy

Gaik Khuan Chuah, Department of Chemistry, National University of Singapore, Kent

Ridge, Singapore 119260, Republic of Singapore

Pere Clapes, Biotransformation and Bioactive Molecules Group, Instituto de Quimica



Andrew J. Collis, GlaxoSmithKline, Biotechnology and Environmental Shared Service,

North Lonsdale Road, Ulverston, Cumbria LA12 9DR, UK

Stefano Colonna, Dipartimento di Scienze Molecolari Applicate ai Biosistemi

(DISMAB), Facolta di Farmacia, Universita degli Studi di Milano, via Venezian 21,

20133 Milano, Italy

Philip Conway, School of Biomolecular and Biomedical Science, University College

Dublin, Belfield, Dublin 4, Ireland

Maria Serrano Correia, Rua Maria Auxiliadora, n�147, 6�andar porta 3, Bairro do

Rosario, P-2750-616 Cascais, Portugal

Marıa-Isabel Covas, Research Unit on Lipids and Cardiovascular Epidemiology, Institut

Municipal d’Investigacio Medica (IMIM). Universitat Pompeu Fabra (CEXS-UPF),

Barcelona, Spain

Yi-jun Dai, Nanjing Engineering Research Center for microbiology, Jiangsu Key

Laboratory for Biodiversity and Biotechnology, College of Life Science, Nanjing

Normal University, 1, Wenyuan Rd, Nanjing 210046, PR China

Philippe Dellis, Synkem, 47 rue de Longvic, 21300 Chenove, France

Paul Devine, Process Research, Merck Research Laboratories, Merck & Co. Inc. Rahway,

NJ, USA

xx List of Contributors

Andrew J. Ellis, School of Chemistry, Manchester Interdisciplinary Biocentre, University

of Manchester, 131 Princess Street, Manchester, M1 7DN, UK

Tadashi Ema, Division of Chemistry and Biochemistry, Graduate School of Natural

Science and Technology, Okayama University, Tsushima, Okayama 700-8530, Japan

Paul Engel, School of Biomolecular and Biomedical Science, University College Dublin,

Belfield, Dublin 4, Ireland

Nobuyoshi Esaki, Institute for Chemical Research, Kyoto University, Uji, Kyoto

611-0011, Japan

Kurt Faber, Department of Chemistry, Organic and Bioorganic Chemistry, University of

Graz, Heinrichstrasse 28, 8010 Graz, Austria

Susana Fernandez, Departamento de Quımica Organica e Inorganica and Instituto

Universitario de Biotecnologıa de Asturias, Universidad de Oviedo, 33006-Oviedo

(Asturias), Spain

Miguel Ferrero, Departamento de Quımica Organica e Inorganica and Instituto

Universitario de Biotecnologıa de Asturias, Universidad de Oviedo, 33006-Oviedo

(Asturias), Spain

Fred Fleitz, Process Research, Merck Research Laboratories, Merck & Co. Inc. Rahway,

NJ, USA

Kam Loon Fow, Department of Chemistry, National University of Singapore, Kent


Aya Fujino, Department of Chemistry, Faculty of Science and Technology, Keio

University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan

Petra Gadler, Department of Chemistry, Organic and Bioorganic Chemistry, University

of Graz, Heinrichstrasse 28, 8010 Graz, Austria

Nicoletta Gaggero, Dipartimento di Scienze Molecolari Applicate ai Biosistemi

(DISMAB), Facolta di Farmacia, Universita degli Studi di Milano, via Venezian 21,

20133 Milano, Italy

Stephane Gastaldi, Laboratoire de Chimie Moleculaire Organique, LCP UMR 6264,

Boite 562, Universite Paul Cezanne, Aix-Marseille III, Faculte des Sciences St Jerome,

Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France

Thierry Gefflaut, Department of Chemistry, Universite Blaise Pascal, Clermont-Ferrand,

France

Oreste Ghisalba, Ghisalba Life Sciences GmbH, Habshagstrasse 8c, CH-4153 Reinach,

Switzerland

Gerard Gil, Laboratoire de Stereochimie Dynamique et Chiralite, ISM2, UMR 6263,

Universite Paul Cezanne, Aix-Marseille III, Faculte des Sciences St Jerome, Avenue

Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France

List of Contributors xxi

Vicente Gotor, Departamento de Quımica Organica e Inorganica and Instituto Universitario

de Biotecnologıa de Asturias, Universidad de Oviedo, 33006-Oviedo (Asturias), Spain

William A. Greenberg, Department of Chemistry, The Scripps Research Institute, 10550

North Torrey Pines Rd., La Jolla, CA 92307, USA

Herfried Griengl, Research Centre Applied Biocatalysis, Petersgasse 14, 8010 Graz, Austria

Gideon Grogan, York Structural Biology Laboratory, Department of Chemistry,

University of York, Heslington, York, YO10 5YW, UK

F. Hamzah, School of Chemical Engineering, Engineering Campus, Universiti Sains

Malaysia, Seri Ampangan, 14300, Nibong Tebal, Penang, Malaysia

Bernhard Hauer, Institute of Technical Biochemistry, University of Stuttgart,

Allmandring 31, 70569 Stuttgart, Germany

Laurence Hecquet, Laboratoire SEESIB, UMR 6504 CNRS, Universite Blaise Pascal,

24 avenue des Landais, 63177 Aubiere, France

Virgil Helaine, Laboratoire SEESIB, UMR 6504 CNRS, Universite Blaise Pascal, 24 ave-

nue des Landais, 63177 Aubiere, France

Richard K. Henderson, GlaxoSmithKline, Centre of Excellence for Sustainability and

Environment, Park Road, Ware, Hertfordshire SG12 0DP, UK

Cheryl Hill, York Structural Biology Laboratory, Department of Chemistry, University of

York, Heslington, York, YO10 5YW, UK

Frank Hollmann, Max-Planck-Institut fur Kohlenforschung, Kaiser-Wilhelm-Platz 1,

45470 Mulheim/Ruhr, Germany

C. Akira Horiuchi, Department of Chemistry, Rikkyo (St.Paul’s) University, Nishi-

Ikebukuro, Toshima-Ku, Tokyo 171-8501, Japan

Rui-Zhen Hou, Key Laboratory for Molecular Enzymology and Engineering of Ministry

of Education, Jilin University, Changchun, 130021, PR China

Yi-Bing Huang, Key Laboratory for Molecular Enzymology and Engineering of Ministry

of Education, Jilin University, Changchun, 130021, PR China

L.A. Hulshof, Eindhoven University of Technology, Laboratory of Macromolecular and

Organic Chemistry, PO Box 513, 5600 MB Eindhoven, The Netherlands

Sayaka Ide, Division of Chemistry and Biochemistry, Graduate School of Natural Science

and Technology, Okayama University, Tsushima, Okayama 700-8530, Japan

Masaya Ikunaka, Fine Chemicals Department, Nagase & Co., Ltd., 5-1, Nihonbashi-

Kobunacho, Chuo-ku, Tokyo 103-8355, Japan

Tomoyuki Inoue, Institute of Microbiology, University of Stuttgart, Allmandring

31, 70569 Stuttgart, Germany

Stephan Jaenicke, Department of Chemistry, National University of Singapore, Kent


xxii List of Contributors

Dick B. Janssen, Biochemical Laboratory, Groningen Biomolecular Sciences and

Biotechnology Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen,

The Netherlands

Jesus Joglar, Biotransformation and Bioactive Molecules Group, Instituto de Quimica



Dimitris Kalaitzakis, Department of Chemistry, University of Crete, Iraklion-Voutes,

71003 Crete, Greece

Azlina Kamaruddin, School of Chemical Engineering, Engineering Campus,

Universiti Sains Malaysia, Seri Ampangan, 14300, Nibong Tebal, Penang,

Malaysia

Bjoern-Arne Kaup, DECHEMA e.V., Karl-Winnacker-Institut, Biochemical

Engineering Group, Theodor-Heuss-Allee 25, 60486 Frankfurt, Germany

Romas J. Kazlauskas, Department of Biochemistry, Molecular Biology & Biophysics

and The Biotechnology Institute, University of Minnesota, 1479 Gortner Avenue, Saint

Paul, MN 55108, USA

Arshdeep Khare, Center for Biocatalysis and Bioprocessing, 2501 Crosspark Road, Suite

C100 MTF, University of Iowa, Iowa City, Iowa, IA 52242-5000, USA

Olha Khymenets, Pharmacology Research Unit, Institut Municipal d’Investigacio

Medica (IMIM), Barcelona, Spain

Piotr Kiełbasinski, Institute for Molecules and Materials, Radboud University Nijmegen,

Toernooiveld 1, NL-6525 ED Nijmegen, The Netherlands

Mahn-Joo Kim, Department of Chemistry, Pohang University of Science and Technology

(POSTECH), San-31, Hyojadong, Pohang 790-784, Korea

Anett Kirschner, Department of Biotechnology and Enzyme Catalysis, Institute of

Biochemistry, Greifswald University, Felix-Hausdorff-Str. 4, 17487 Greifswald,

Germany

Matthias Kittelmann, GDC/PSB/Bioreactions, Novartis Institutes of Biomedical

Research (NIBR), Novartis Pharma AG, CH-4002 Basel, Switzerland

Soo-Byung Ko, Department of Chemistry, Pohang University of Science and Technology


Yoshinori Kondo, Department of Biomolecular Science, Gifu University, Yanagido 1-1,

Gifu 501-1193, Japan

Birgit Kosjek, Process Research, Merck Research Laboratories, Merck & Co. Inc.

Rahway, NJ, USA

Udo Kragl, Institut fur Chemie, Universitat Rostock, Albert-Einstein-Str. 3a, 18059

Rostock, Germany

List of Contributors xxiii

Vladimır Kren, Institute of Microbiology, Center of Biocatalysis and Biotransformations,

Academy of Sciences of the Czech Republic, Vıdenska 1083, CZ-142 20 Prague 4, Czech

Republic

Anton Kuhn, GDC/PSB/Bioreactions, Novartis Institutes of Biomedical Research

(NIBR), Novartis Pharma AG, CH-4002 Basel, Switzerland

Jurgen Kuhnol, GDC/PSB/Separations, NIBR, Novartis Pharma AG, CH-4002 Basel,

Switzerland

Andrew S. Lamm, Center for Biocatalysis and Bioprocessing, 2501 Crosspark Road,

Suite C100 MTF, University of Iowa, Iowa City, Iowa, IA 52242-5000, USA

Jan von Langermann, Max-Planck-Institut fur Dynamik komplexer technischer

Systeme, Physikalisch-Chemische Grundlagen der Prozesstechnik, Sandtorstr.1 D-39106

Magdeburg, Germany

Peter C.K. Lau, Biotechnology Research Institute, National Research Council Canada,

Montreal, Quebec H4P 2R2, Canada

Marielle Lemaire, Laboratoire SEESIB, UMR 6504 CNRS, Universite Blaise Pascal, 24

avenue des Landais 63177 Aubiere cedex, France

Renata P. Limberger, State University of Campinas, Institute of Chemistry, CP 6154,

13084-971, Campinas-SP, Brazil

Guo-Qiang Lin, Laboratory of Biocatalysis and Bioprocessing, State Key Laboratory of

Bioreactor Engineering, East China University of Science and Technology, Shanghai

200237, PR China

Wen-Ya Lu, Laboratory of Biocatalysis and Bioprocessing, State Key Laboratory of


200237, PR China

Maja Majeric Elenkov, Laboratory for Stereoselective Catalysis and Biocatalysis, Ru�der

Boskovic Institute, Bijenicka c. 54, 10002 Zagreb, Croatia

Kathleen H. McClean, C-Tech Innovation Ltd, Capenhurst Technology Park,

Capenhurst, Chester, CH1 6EH, UK

Annett Mell, Institut fur Chemie, Universitat Rostock, Albert-Einstein-Str. 3a, 18059

Rostock, Germany

J. Meuldijk, Eindhoven University of Technology, Laboratory of Macromolecular and

Organic Chemistry, PO Box 513, 5600 MB Eindhoven, The Netherlands

Hisaaki Mihara, Department of Biotechnology, Institute of Science and Engineering,

College of Life Sciences, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan

Marco-Antonio Mirata, DECHEMA e.V., Karl-Winnacker-Institut, Biochemical

Engineering Group, Theodor-Heuss-Allee 25, 60486 Frankfurt, Germany

xxiv List of Contributors

Koichi Mitsukura, Department of Biomolecular Science, Gifu University, Yanagido 1-1,


Jeffrey Moore, Process Research, Merck Research Laboratories, Merck & Co. Inc.

Rahway, NJ, USA

Paulo J. S. Moran, State University of Campinas, Institute of Chemistry, CP 6154,


Krista Morley, Process Research, Merck Research Laboratories, Merck & Co. Inc.

Rahway, NJ, USA

Musa M. Musa, Department of Chemistry and of Biochemistry and Molecular Biology,

University of Georgia, Athens, GA 30602, USA

Toru Nagasawa, Department of Biomolecular Science, Gifu University, Yanagido 1-1,


S.F.G.M. van Nispen, Eindhoven University of Technology, Laboratory of Macromolecular

and Organic Chemistry, PO Box 513, 5600 MB Eindhoven, The Netherlands

Louise C. Nolan, School of Biomolecular and Biomedical Science, Conway Institute for

Biomolecular and Biomedical Research, National University of Ireland, University

College Dublin, Ardmore House, Belfield, Dublin 4, Republic of Ireland

Kevin E. O’Connor, School of Biomolecular and Biomedical Science, Conway Institute

for Biomolecular and Biomedical Research, National University of Ireland, University

College Dublin, Ardmore House, Belfield, Dublin 4, Republic of Ireland

Lukas Oberer, Analytical and Imaging Sciences, Novartis Institutes of Biomedical

Research, Novartis Pharma AG, CH-4002 Basel, Switzerland

Nobuyasu Okita, Division of Chemistry and Biochemistry, Graduate School of Natural


Eckhard Paetzold, Leibniz-Institut fur Katalyse, A.-Einstein-Str. 29a,18059 Rostock

Germany

Michael Page, Department of Chemical and Biological Sciences, The University of

Huddersfield, Huddersfield, HD1 3DH, UK

Francesca Paradisi, School of Chemistry and Chemical Biology, University College

Dublin, Belfield, Dublin 4, Ireland

Serge Parel, Biofocus DPI AG, Gewerbestrasse 16, CH-4123 Allschwil, Switzerland

Teodor Parella, Servei de Ressonancia Magnetica Nuclear, Universitat Autonoma de

Barcelona, 08193 Bellaterra, Barcelona, Spain

Jaiwook Park, Department of Chemistry, Pohang University of Science and Technology


Sara Pellegrino, Dipartimento di Scienze Molecolari Applicate ai Biosistemi (DISMAB),

Facolta di Farmacia, Universita degli Studi di Milano, via Venezian 21, 20133 Milano, Italy

List of Contributors xxv

Fabio Pezzotti, ECBB, ICMMO, Univ Paris-Sud, UMR 8182, F-91405 Orsay, France

Robert S. Phillips, Department of Chemistry and of Biochemistry and Molecular Biology,

University of Georgia, Athens, GA 30602, USA

Umberto Piantini, Institute of Life Technologies, University of Applied Sciences Valais,

Route du Rawyl 47, 1950 Sion, Switzerland

David Pollard, Process Research, Merck Research Laboratories, Merck & Co. Inc.

Rahway, NJ, USA

Monique Ponelle, Analytical and Imaging Sciences, NIBR, Novartis Pharma AG,

CH-4002 Basel, Switzerland

Manfred T. Reetz, Max-Planck-Institut fur Kohlenforschung, Kaiser-Wilhelm-Platz 1,


Renate Reiss, School of Chemistry, Manchester Interdisciplinary Biocentre, University of

Manchester, 131 Princess Street, Manchester, M1 7DN, UK

Sergio Riva, Istituto di Chimica del Riconoscimento Molecolare, C.N.R., Via Mario


Chris Roberge, Process Research, Merck Research Laboratories, Merck & Co. Inc.

Rahway, NJ, USA

J. Augusto R. Rodrigues, State University of Campinas, Institute of Chemistry, CP 6154,


John P. N. Rosazza, Center for Biocatalysis and Bioprocessing, 2501 Crosspark Road,

Suite C100 MTF, University of Iowa, Iowa City, Iowa, IA 52242-5000, USA

Monika Rusek, Max-Planck-Institut fur Kohlenforschung, Kaiser-Wilhelm-Platz 1,


Floris P. J. T. Rutjes, Institute for Molecules and Materials, Radboud University

Nijmegen, Toernooiveld 1, NL-6525 ED Nijmegen, The Netherlands

Emmanuelle Sagot, Department of Chemistry, Universite Blaise Pascal, Clermont-

Ferrand, France

Francesca Sagui, Istituto di Chimica del Riconoscimento Molecolare, C.N.R., Via Mario


Takashi Sakai, Division of Chemistry and Biochemistry, Graduate School of Natural


Soth Samreth, Fournier Pharma, 50 rue de Dijon, 21121 Daix, France

Christopher K. Savile, Department of Biochemistry, Molecular Biology & Biophysics

and The Biotechnology Institute, University of Minnesota, 1479 Gortner Avenue, Saint

Paul, MN 55108 USA

Adrian Scaffidi, Chemistry M313, School of Biomedical, Biomolecular and Chemical

Sciences, University of Western Australia, Crawley, WA 6009, Australia

xxvi List of Contributors

Andreas Schmid, Laboratory of Chemical Biotechnology, Faculty of Biochemical and

Chemical Engineering, TU Dortmund, Emil-Figge-Strasse 66, 44221 Dortmund, Germany

Jens Schrader, DECHEMA e.V., Karl-Winnacker-Institut, Biochemical Engineering

Group, Theodor-Heuss-Allee 25, 60486 Frankfurt, Germany

Frank Schulz, Max-Planck-Institut fur Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470

Mulheim/Ruhr, Germany

Ioulia Smonou, Department of Chemistry, University of Crete, Iraklion-Voutes, 71003

Crete, Greece

Timothy Snape, School of Chemistry, Manchester Interdisciplinary Biocentre, University

of Manchester, 131 Princess Street, Manchester, M1 7DN, UK

Georg A. Sprenger, Institute of Microbiology, University of Stuttgart, Allmandring 31,

70569 Stuttgart, Germany

Robert V Stick, Chemistry M313, School of Biomedical, Biomolecular and Chemical

Sciences, University of Western Australia, Crawley, WA 6009, Australia

Matthew Stirling, Department of Chemical and Biological Sciences, The University of

Huddersfield, Huddersfield, HD1 3DH, UK

Takeshi Sugai, Faculty of Pharmacy, Keio University, 1-5-30, Shibakoen, Minato-ku,

Tokyo 105-8512, Japan

Peter Sutton, GlaxoSmithKline, Synthetic Chemistry, Gunnels Wood Road, Stevenage,

Hertfordshire SG1 2NY, UK

Andreas Taglieber, Max-Planck-Institut fur Kohlenforschung, Kaiser-Wilhelm-Platz 1,


Lixia Tang, Biochemical Laboratory, Groningen Biomolecular Sciences and

Biotechnology Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen,

The Netherlands

Alan Taylor, Centre for Material Science, University of Central Lancashire, Preston

Lancashire, UK

David Tellers, Process Research, Merck Research Laboratories, Merck & Co. Inc.

Rahway, NJ, USA

Helene Therisod, ECBB, ICMMO, Univ Paris-Sud, UMR 8182, F-91405 Orsay,

France

Michel Therisod, ECBB, ICMMO, Univ Paris-Sud, UMR 8182, F-91405 Orsay, France

Ai-Ming Tong, Laboratory of Biocatalysis and Bioprocessing, State Key Laboratory of


200237, PR China

Rafael de la Torre, Pharmacology Research Unit, Institut Municipal d’Investigacio

Medica (IMIM), Barcelona, Spain

List of Contributors xxvii

Matthew Truppo, Process Research, Merck Research Laboratories, Merck & Co. Inc.

Rahway, NJ, USA

Nicholas J. Turner, School of Chemistry, Manchester Interdisciplinary Biocentre,

University of Manchester, 131 Princess Street, Manchester, M1 7DN, UK

Cleber V. Ursini, State University of Campinas, Institute of Chemistry, CP 6154, 13084-

971, Campinas-SP, Brazil

Takamitsu Utsukihara, Department of Chemistry, Rikkyo (St.Paul’s) University, Nishi-

Ikebukuro, Toshima-Ku, Tokyo 171-8501, Japan

J.A.J.M. Vekemans, Eindhoven University of Technology, Laboratory of

Macromolecular and Organic Chemistry, PO Box 513, 5600 MB Eindhoven, The

Netherlands

Claire Vieille, Biochemistry and Molecular Biology, Michigan State University, East

Lansing, MI 48824, USA

Shaozhao Wang, Biotechnology Research Institute, National Research Council Canada,


Marloes A. Wijdeven, Institute for Molecules and Materials, Radboud University

Nijmegen, Toernooiveld 1, NL-6525 ED Nijmegen, The Netherlands

Chi-Huey Wong, Department of Chemistry, The Scripps Research Institute, 10550 North

Torrey Pines Rd., La Jolla, CA 92307, USA

Matthias Wust, Institute of Life Technologies, University of Applied Sciences Valais,

Route du Rawyl 47, 1950 Sion, Switzerland

Li Xu, Key Laboratory for Molecular Enzymology and Engineering of Ministry of

Education, Jilin University, Changchun, 130021, PR China

Jian-He Xu, Laboratory of Biocatalysis and Bioprocessing, State Key Laboratory of


200237, PR China

Hitomi Yamaguchi, Research & Development Center, Nagase & Co., Ltd., 2-2-3,

Murotani, Nishi-ku, Kobe 651-2241, Japan

Jianzhong Yang, Biotechnology Research Institute, National Research Council Canada,


Toyokazu Yoshida, Department of Biomolecular Science, Gifu University, Yanagido

1-1, Gifu 501-1193, Japan

Hui-Lei Yu, Laboratory of Biocatalysis and Bioprocessing, State Key Laboratory of


200237, PR China

Sheng Yuan, Nanjing Engineering Research Center for microbiology, Jiangsu Key

Laboratory for Biodiversity and Biotechnology, College of Life Science, Nanjing

Normal University, 1, Wenyuan Rd, Nanjing 210046, PR China

xxviii List of Contributors

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