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Dr John Whittall, Centre of Excellence for Biocatalysis, Biotransformations and Biocatalytic Manufacture (CoEBio3), Manchester Interdisciplinary Biocentre, University of Manchester, UK.
Dr Peter W Sutton, Senior Scientist, GlaxoSmithKline Research and Development Limited, UK.
Dr Wolfgang Kroutil, Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Austria.
List of Contributors ix
Abbreviations xxi
1 Considerations for the Application of Process Technologies in Laboratory- and Pilot-Scale Biocatalysis for Chemical Synthesis 1
1.1 Introduction 1
1.2 Process Intensification and Proposed Scale-Up Concept 2
1.3 Enabling Technologies 5
1.4 Enhancing Technologies 20
1.5 Conclusion 28
References 28
2 Cytochrome P450 (CYP) Progress in Biocatalysis for Synthetic Organic Chemistry 31
2.1 Introduction 31
2.2 CYP Development 32
2.3 Recent Developments 34
2.4 Conclusion 41
References 41
3 Use of Hydrolases and Related Enzymes for Synthesis 43
3.1 Continuous-Flow Reactor-Based Enzymatic Synthesis of Phosphorylated Compounds on a Large Scale 43
3.2 Deracemization of sec-Alcohols via Enantio-Convergent Hydrolysis of rac-Sulfate Esters 45
3.3 Dynamic Kinetic Resolution of a Primary Amine by an Efficient Bifunctional Pd-CALB Hybrid Catalyst. A Metalloenzyme Mimic for Enhanced Cooperative Catalysis 50
3.4 Highly Efficient DKR of Secondary 1-Phenylethanol Derivatives Using a Low-Cost Solid Super Acid as Racemization Catalyst 53
3.5 Identification of New Biocatalysts for the Enantioselective Conversion of Tertiary Alcohols 58
3.6 Enzyme-Catalyzed Hydrolysis of Bicycloheptane Diester to Monoester 60
3.7 Double Mutant Lipase with Enhanced Activity and Enantioselectivity for Bulky Secondary Alcohols 64
3.8 Stereoselective Synthesis of ß-Amino Acids by Hydrolysis of an Aryl-Substituted Dihydropyrimidine by Hydantoinases 68
References 72
4 Non-Redox Lyases and Transferases for C-C, C-O, C-S, and C-N Bond Formation 75
4.1 Regioselective Enzymatic Carboxylation of Phenols and Hydroxystyrenes Employing Co-Factor-Independent Decarboxylases 75
4.2 Stetter Reactions Catalyzed by Thiamine Diphosphate-Dependent Enzymes 81
4.3 Asymmetric Michael-Type Additions of Acetaldehyde to Nitroolefins Catalyzed by 4-Oxalocrotonate Tautomerase (4-OT) Yielding Valuable ¿-Nitroaldehydes 85
4.4 Michael-Type Addition of Aldehydes to ß-Nitrostyrenes by Whole Cells of Escherichia coli Expressing 4-Oxalocrotonate Tautomerase (4-OT) 91
4.5 Norcoclaurine Synthases for the Biocatalytic Synthesis of Tetrahydroisoquinolines 95
4.6 Streptavidin-Based Artificial Metallo-Annulase for the Enantioselective Synthesis of Dihydroisoquinolones 101
4.7 Regiospecific Benzylation of Tryptophan and Derivatives Catalyzed by a Fungal Dimethylallyl Transferase 102
4.8 Enantioselective Michael Addition of Water Using Rhodococcus Rhodochrous ATCC 17895 106
4.9 Sulfation of Various Compounds by an Arylsulfotransferase from Desulfitobacterium hafniense and Synthesis of 17ß-Estradiol-3-Sulfate 111
4.10 Asymmetric Synthesis of Cyclopropanes and Benzosultams via Enzyme-Catalyzed Carbenoid and Nitrenoid Transfer in E. coli Whole Cells 113
4.11 Biocatalytic Production of Novel Glycolipids 118
4.12 Enzymatic Synthesis of 8-Aza- and 8-Aza-7-Deazapurine 2¿-Deoxyribonucleosides 124
4.13 Phenylalanine Ammonia Lyase-Catalyzed Asymmetric Hydroamination for the Synthesis of L-Amino Acids 128
References 130
5 Oxidations 135
5.1 Semi-Preparative-Scale Drug Metabolite Synthesis with Human Flavin Monooxygenases 135
5.2 Biobased Synthesis of Industrially Relevant Nitriles by Selective Oxidative Decarboxylation of Amino Acids by Vanadium Chloroperoxidase 139
5.3 Terminal Oxygenation of Fatty Acids by a CYP153A Fusion Construct Heterologously Expressed in E. coli 142
5.4 Enantioselective Oxidative C-C Bond Formation in Isoquinoline Alkaloids Employing the Berberine Bridge Enzyme 144
5.5 Oxidation of Aldehydes Using Alcohol Dehydrogenases 148
5.6 MAO-Catalyzed Deracemization of Racemic Amines for the Synthesis of Pharmaceutical Building Blocks 150
5.7 Synthesis of (S)-Amines by Chemo-Enzymatic Deracemization Using an (R)-Selective Amine Oxidase 153
5.8 Selective Oxidation of Diols into Lactones under Aerobic Conditions Using a Laccase-TEMPO Catalytic System in Aqueous Medium 156
References 160
6 Reductions 163
6.1 Tetrahydroxynaphthalene Reductase: Broad Substrate Range of an NADPH-Dependent Oxidoreductase Involved in Reductive Asymmetric Naphthol Dearomatization 163
6.2 Chemoenzymatic Synthesis of Diastereo- and Enantiomerically Pure 2,6-Disubstituted Piperidines via Regioselective Monoamination of 1,5-Diketones 167
6.3 Asymmetric Amination of Ketones Employing ¿-TAs in Organic Solvents 171
6.4 Stereoselective Synthesis of (R)-Profen Derivatives by the Enoate Reductase YqjM 176
6.5 Productivity Improvement of the Bioreduction of a,ß-Unsaturated Aldehydes by Coupling of the In Situ Substrate Feeding Product Removal (SFPR) Strategy with Isolated Enzymes 181
6.6 Reduction of Imines by Recombinant Whole-Cell E. coli Biocatalysts Expressing Imine Reductases (IREDs) 186
References 191
7 Halogenation and Dehalogenation 193
7.1 Site-Directed Mutagenesis Changes the Regioselectivity of the Tryptophan 7-Halogenase PrnA 193
7.2 Controlling Enantioselectivity of Halohydrin Dehalogenase from Arthrobacter sp. Strain AD2, Revealed by Structure-Guided Directed Evolution 197
7.3 Enzymatic Production of Chlorothymol and its Derivatives by Halogenation of the Phenolic Monoterpenes Thymol and Carvacrol with Chloroperoxidase 201
7.4 Halogenation of Non-Activated Fatty Acyl Groups by a Trifunctional Non-Heme Fe(II)-Dependent Halogenase 204
References 211
8 Cascade Reactions 213
8.1 Synthetic Cascades via a Combination of Artificial Metalloenzymes with Monoamine Oxidases (MAO-Ns) 213
8.2 Amination of Primary Alcohols via a Redox-Neutral Biocascade 215
8.3 Biocatalytic Synthesis of a Diketobornane as a Building Block for Bifunctional Camphor Derivatives 218
8.4 Three Enzyme-Catalyzed Redox Cascade for the Production of a Carvo-Lactone 222
8.5 Preparation of Homoallylic Alcohols via a Chemoenzymatic One-Pot Oxidation-Allylation Cascade 226
8.6 Cascade Biotransformations via Enantioselective Reduction, Oxidation, and Hydrolysis: Preparation of (R)-d-Lactones from 2-Alkylidenecyclopentanones 230
8.7 One-Pot Tandem Enzymatic Reactions for Efficient Biocatalytic Synthesis of D-Fructose-6-Phosphate and Analogs 232
8.8 Efficient One-Pot Tandem Biocatalytic Process for a Valuable Phosphorylated C8 D-Ketose: D-Glycero-D-Altro-2-Octulose 8-Phosphate 239
8.9 Chemoenzymatic Synthesis of (S)-1,2,3,4-Tetrahydroisoquinoline-3-Carboxylic Acid by PAL-Mediated Amination and Pictet-Spengler Cyclization 243
8.10 ¿-TA/MAO Cascade for the Regio- and Stereoselective Synthesis of Chiral 2,5-Disubstituted Pyrrolidines 246
References 249
9 Biocatalysis for Industrial Process Development 253
9.1 Efficient Synthesis of (S)-1-(5-Fluoropyrimidin-2-yl)ethylamine Hydrochloride Salt Using an ¿-Transaminase Biocatalyst in a Two-Phase System 253
9.2 Preparative-scale Production of a Chiral, Bicyclic Proline Analog Intermediate for Boceprevir 257
9.3 Focused Carbonyl Reductase Screening for Rapid Gram Supply of Highly Enantioenriched Secondary Alcohol Libraries 260
9.4 A Rapid, Inexpensive and Colorimetric High-throughput Assay Format for Screening Commercial Ketoreductase Panels, Providing Indication of Substrate Scope, Co-factor Specificity and Enantioselectivity 266
9.5 Stereoselective Production of (R)-3-quinuclidinol Using Recombinant Escherichia coli Whole Cells Overexpressing 3-Quinuclidinone Reductase and a Co-factor Regeneration System 273
9.6 Preparation of N-Boc-D-Serine Using a Coupled D-Acylase/Racemase Enzyme System 275
9.7 Scale-up of a Biocatalytic Oxidase in a Dynamically Mixed Tubular Flow Reactor 279
References 282
Index 285
Syed T. Ahmed School of Chemistry, Manchester Institute of Biotechnology, The University of Manchester, UK
Ian Archer Ingenza Ltd, Roslin BioCentre, UK
Frances H. Arnold Division of Chemistry and Chemical Engineering, California Institute of Technology, USA
Robert Ashe AM Technology, UK
Lara Babich Van't Hoff Institute for Molecular Sciences, University of Amsterdam, The Netherlands
Jan-E. Bäckvall Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden
Maria Bawn Prozomix Limited, UK
Beatrice Bechi School of Chemistry, Manchester Institute of Biotechnology, The University of Manchester, UK
Gary Black Northumbria University, Department of Applied Science, UK
Fabrizio Bonina Institute of Pharmaceutical Sciences, Albert Ludwigs University of Freiburg, Germany
Uwe T. Bornscheuer Institute of Biochemistry, Department of Biotechnology and Enzyme Catalysis, University of Greifswald, Germany
Elisabetta Brenna Department of Chemistry, Material and Chemical Engineering "G. Natta," Polytechnic University of Milan, Italy
Aleksandra Bury Van't Hoff Institute for Molecular Sciences, University of Amsterdam, The Netherlands
Andrada But Biobased Commodity Chemistry, Wageningen University, The Netherlands
Simon Charnock Prozomix Limited, UK
Bi-Shuang Chen Department of Biotechnology, Delft University of Technology, The Netherlands
Yong-Jun Chen Department of Chemical and Biological Engineering, Zhejiang University, China
Pere Clapés Biotransformation and Bioactive Molecules Group, Institute of Advanced Chemistry of Catalonia (IQAC-CSIC), Spain
Thomas Classen Institute of Bioorganic Chemistry, Heinrich Heine University Düsseldorf, Germany
Marine Debacker Clermont University, Blaise Pascal University, ICCF, Clermont-Ferrand, France; CNRS, UMR 6296, France
Tom Desmet Centre for Industrial Biotechnology and Biocatalysis, Faculty of Bioscience Engineering, Ghent University, Belgium
Karel De Winter Centre for Industrial Biotechnology and Biocatalysis, Faculty of Bioscience Engineering, Ghent University, Belgium
Griet Dewitte Centre for Industrial Biotechnology and Biocatalysis, Faculty of Bioscience Engineering, Ghent University, Belgium
Alba Díaz-Rodríguez Department of Organic and Inorganic Chemistry, Asturias Institute of Biotechnology, University of Oviedo, Spain
Carola Dresen Institute of Pharmaceutical Sciences, Albert Ludwigs University of Freiburg, Germany
Richard Duncan Prozomix Limited, UK
Marc Dürrenberger Department of Inorganic Chemistry, University of Basel, Switzerland
Tadashi Ema Division of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University, Japan
Ulrike Engel Institute of Process Engineering in Life Sciences, Section II: Technical Biology, Karlsruhe Institute of Technology, Germany
Roman S. Esipov Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Russia
Kurt Faber Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Austria
Christopher C. Farwell Division of Chemistry and Chemical Engineering, California Institute of Technology, USA
James Finnigan Prozomix Limited, UK
Christine Fuchs Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Austria
Michael Fuchs Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Austria
Anna Fryszkowska Merck Research Laboratories, USA
Eduardo García-Junceda Department of Bioorganic Chemistry, Institute of General Organic Chemistry, Spain
Gilda Gasparini AM Technology, UK
Francesco G. Gatti Department of Chemistry, Material and Chemical Engineering "G. Natta," Polytechnic University of Milan, Italy
Edzard M. Geertsema Department of Pharmaceutical Biology, Groningen Research Institute of Pharmacy, University of Groningen, The Netherlands
Laura Getrey DECHEMA Research Institute, Germany
Diego Ghislieri School of Chemistry, Manchester Institute of Biotechnology, The University of Manchester, UK
Silvia M. Glueck Austrian Centre of Industrial Biotechnology, Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Austria
Michael Golden AstraZeneca, Chemical Development, UK
Animesh Goswami Chemical Development, Bristol-Myers Squibb, USA
Vicente Gotor Department of Organic and Inorganic Chemistry, Asturias Institute of Biotechnology, University of Oviedo, Spain
Vicente Gotor-Fernández Department of Organic and Inorganic Chemistry, Asturias Institute of Biotechnology, University of Oviedo, Spain
Johannes Gross Austrian Centre of Industrial Biotechnology, Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Austria
Christine Guérard-Hélaine Clermont University, Blaise Pascal University, ICCF, Clermont-Ferrand, France; CNRS, UMR 6296, France
Zhiwei Guo Chemical Development, Bristol-Myers Squibb, USA
Karl P. J. Gustafson Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden
Helen C. Hailes Department of Chemistry, Christopher Ingold Laboratories, University College London, UK
Ulf Hanefeld Department of Biotechnology, Delft University of Technology, The Netherlands
Steven P. Hanlon F. Hoffmann-La Roche Ltd., Switzerland
Aloysius F. Hartog Van't Hoff Institute for Molecular Sciences, University of Amsterdam, The Netherlands
Bernhard Hauer Institute of Technical Biochemistry, University of Stuttgart, Germany
Rachel S. Heath School of Chemistry, Manchester Institute of Biotechnology, The University of Manchester, UK
Virgil Hélaine Clermont University, Blaise Pascal University, ICCF, Clermont-Ferrand, France; CNRS, UMR 6296, France
Susanne Herter Institute of Biochemistry, Department of Biotechnology and Enzyme Catalysis, University of Greifswald, Germany
Matthew R. Hickey Chemical Development, Bristol-Myers Squibb, USA
Michael Hofer Fraunhofer Institute for Interfacial Engineering and Biotechnology, Institute branch Straubing, BioCat - Bio-, Chemo- and Electrocatalysis, Germany
Frank Hollmann Department of Biotechnology, Delft University of Technology, The Netherlands
Dirk Holtmann DECHEMA Research Institute, Germany
Karen Holt-Tiffin Dr Reddy's Laboratories Ltd, Chirotech Technology Centre, UK
Roger M. Howard Pfizer Ltd, Chemical Research & Development, UK
Gjalt Huisman Codexis Inc, USA
Shahed Hussain School of Chemistry, Manchester Institute of Biotechnology, The University of Manchester, UK
Syed Masood Husain Institute of Pharmaceutical Sciences, Albert-Ludwigs-Universität Freiburg, Germany
Todd K. Hyster Department of Inorganic Chemistry, University of Basel, Switzerland; Department of Chemistry, Colorado State University, USA
Ed Jones C-Tech Innovation Ltd, UK
Predrag Jovanovic Department of Organic Chemistry, Faculty of Pharmacy, University of Belgrade, Serbia
Shusuke Kamata Division of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University, Japan
Elena Kasparyan Institute of Pharmaceutical Sciences, Albert Ludwigs University of Freiburg, Germany
Hans Kierkels DSM Innovative Synthesis BV, The Netherlands
Matthias Kittelmann NovartisPharma AG, Switzerland
Livia Knörr Department of Inorganic Chemistry, University of Basel, Switzerland
Valentin Köhler Department of Inorganic Chemistry, University of Basel, Switzerland
Pieter de Koning Dr Reddy's Laboratories Ltd, Chirotech Technology Centre, UK
Robert Kourist Junior Research Group for Microbial Biotechnology, Ruhr-University Bochum, Germany
Thomas Krieg DECHEMA Research Institute, Germany
Wolfgang Kroutil Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Austria
Jim Lalonde Codexis Inc, USA
Eleanor D. Lamming Department of Chemistry, Christopher Ingold Laboratories, University College London, UK
Alexander Lang General Biochemistry, Dresden University of Technology, Germany
Iván Lavandera Department of Organic and Inorganic Chemistry, Asturias Institute of Biotechnology, University of Oviedo, Spain
Friedemann Leipold School of Chemistry, Manchester Institute of Biotechnology, The University of Manchester, UK
Marielle Lemaire Clermont University, Blaise Pascal University, ICCF, Clermont-Ferrand, France; CNRS, UMR 6296, France
Jerôme Le Nôtre Biobased Commodity Chemistry, Wageningen University, The Netherlands
Shu-Ming Li Institute of Pharmaceutical Biology and Biotechnology, Philipp University of Marburg, Germany
Zhi Li Department of...
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