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Provides clear and comprehensive coverage of recently developed applied biocatalysis for synthetic organic chemists with an emphasis to promote green chemistry in pharmaceutical and process chemistry This book aims to make biocatalysis more accessible to both academic and industrial synthetic organic chemists. It focuses on current topics within the applied industrial biocatalysis field and includes short but detailed experimental methods on timely novel biocatalytic transformations using new enzymes or new methodologies using known enzymes. The book also features reactions that are "expanding…mehr
Provides clear and comprehensive coverage of recently developed applied biocatalysis for synthetic organic chemists with an emphasis to promote green chemistry in pharmaceutical and process chemistry This book aims to make biocatalysis more accessible to both academic and industrial synthetic organic chemists. It focuses on current topics within the applied industrial biocatalysis field and includes short but detailed experimental methods on timely novel biocatalytic transformations using new enzymes or new methodologies using known enzymes. The book also features reactions that are "expanding and making the enzyme toolbox available to chemists"--providing readers with comprehensive methodology and detailed key sourcing information of a wide range of enzymes. Chapters in Applied Biocatalysis: The Chemist's Enzyme Toolkit are organized by reaction type and feature a short introductory section describing the current state of the art for each example. Much of the book focuses on processes for which the enzymes are readily available so that organic chemists can synthesize appropriate quantities of chemicals with available materials in a standard chemical laboratory. Advanced methods are included to present examples of new enzymes that might encourage collaboration with suppliers or academic groups and that will educate chemists of rapidly expanding future possibilities. * Focuses on current topics within the applied industrial biocatalysis field * Offers experimental methods on novel biocatalytic transformations using new enzymes or new methodology using known enzymes * Covers the hot topics of enzyme and chemoenzymatic cascades and biocatalysis in flow * Edited by noted experts from both academia and industry with years of experience in the field of biocatalysis--particularly, the industrial applications of enzymes Written for synthetic organic chemists working in all industries but especially the pharmaceutical industry and for those in academia with an eye for biocatalysis, Applied Biocatalysis: The Chemist's Enzyme Toolkit will also benefit academic groups in chemistry and related sciences that are using enzymes for synthetic purposes, as well as those working in the area of enzymology and molecular biology.
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Autorenporträt
John Whittall, PhD, works at the Centre of Excellence for Biocatalysis, Biotransformations and Biocatalytic Manufacture (CoEBio3), Manchester Institute of Biotechnology, University of Manchester, UK. Peter W. Sutton, PhD, was Scientific Investigator, GlaxoSmithKline Research and Development Limited, UK, now R&D Director at GlycoScience S.L., Barcelona, Spain.
Inhaltsangabe
Abbreviations xi
1 Directed Evolution of Enzymes Driving Innovation in API Manufacturing at GSK 1
1.1 Introduction 1
1.2 Drug Development Stages 3
1.3 Enzyme Panels 6
1.4 Enzyme Engineering 10
1.5 Case Studies 18
1.6 Outlook 22
2 Survey of Current Commercial Enzyme and Bioprocess Service Providers 27
2.1 Commercial Enzyme Suppliers/Distributors 28
2.2 Bioprocess Service Providers 92
2.3 Chemical Transformations of Selected Commercially Available Enzymes 103
3 Imine Reductases 135
3.1 Imine Reductase-Catalysed Enantioselective Reductive Amination for the Preparation of a Key Intermediate to Lysine-Specific Histone Demethylase 1 (LSD1) Inhibitor GSK2879552 135
3.2 Expanding the Collection of Immine Reductases Towards a Stereoselective Reductive Amination 138
3.3 Asymmetric Synthesis of the Key Intermediate of Dextromethorphan Catalysed by an Imine Reductase 143
3.4 Identification of Imine Reductases for Asymmetric Synthesis of 1-Aryl-Tetrahydroisoquinolines 148
3.5 Preparation of Imine Reductases at 15 L Scale and Their Application in Asymmetric Piperazine Synthesis 156
3.6 Screening of Imine Reductases and Scale-Up of an Oxidative Deamination of an Amine for Ketone Synthesis 162
4 Transaminases 165
4.1 A Practical Dynamic Kinetic Transamination for the Asymmetric Synthesis of the CGRP Receptor Antagonist Ubrogepant 165
4.2 Asymmetric Biosynthesis of L-Phosphinothricin by Transaminase 168
4.3 Application of In Situ Product Crystallisation in the Amine Transaminase from Silicibacter pomeroyi-Catalysed Synthesis of (S)-1-(3-Methoxyphenyl)ethylamine 173
4.4 Enantioselective Synthesis of Industrially Relevant Amines Using an Immobilised omega-Transaminase 178
4.5 Amination of Sugars Using Transaminases 182
4.6 Converting Aldoses into Valuable omega-Amino Alcohols Using Amine Transaminases 187
5 Other Carbon-Nitrogen Bond-Forming Biotransformations 193
5.1 Biocatalytic N-Acylation of Anilines in Aqueous Media 193
5.2 Enantioselective Enzymatic Hydroaminations for the Production of Functionalised Aspartic Acids 196
5.3 Biocatalytic Asymmetric Aza-Michael Addition Reactions and Synthesis of L-Argininosuccinate by Argininosuccinate Lyase ARG4-Catalysed Aza-Michael Addition of L-Arginine to Fumarate 204
5.4 Convenient Approach to the Biosynthesis of C2,C6-Disubstituted Purine Nucleosides Using E. coli Purine Nucleoside Phosphorylase and Arsenolysis 211
5.5 Production of L- and D-Phenylalanine Analogues Using Tailored Phenylalanine Ammonia-Lyases 215
5.6 Asymmetric Reductive Amination of Ketones Catalysed by Amine Dehydrogenases 221
5.7 Utilisation of Adenylating Enzymes for the Formation of N-Acyl Amides 231
6 Carbon-Carbon Bond Formation or Cleavage 237
6.1 Improved Enzymatic Method for the Synthesis of (R)-Phenylacetyl Carbinol 237
6.2 Tertiary Alcohol Formation Catalysed by a Rhamnulose-1-Phosphate Aldolase : Dendroketose-1-Phosphate Synthesis 241
6.3 Easy and Robust Synthesis of Substituted L-Tryptophans with Tryptophan Synthase from Salmonella enterica 247
1 Directed Evolution of Enzymes Driving Innovation in API Manufacturing at GSK 1
1.1 Introduction 1
1.2 Drug Development Stages 3
1.3 Enzyme Panels 6
1.4 Enzyme Engineering 10
1.5 Case Studies 18
1.6 Outlook 22
2 Survey of Current Commercial Enzyme and Bioprocess Service Providers 27
2.1 Commercial Enzyme Suppliers/Distributors 28
2.2 Bioprocess Service Providers 92
2.3 Chemical Transformations of Selected Commercially Available Enzymes 103
3 Imine Reductases 135
3.1 Imine Reductase-Catalysed Enantioselective Reductive Amination for the Preparation of a Key Intermediate to Lysine-Specific Histone Demethylase 1 (LSD1) Inhibitor GSK2879552 135
3.2 Expanding the Collection of Immine Reductases Towards a Stereoselective Reductive Amination 138
3.3 Asymmetric Synthesis of the Key Intermediate of Dextromethorphan Catalysed by an Imine Reductase 143
3.4 Identification of Imine Reductases for Asymmetric Synthesis of 1-Aryl-Tetrahydroisoquinolines 148
3.5 Preparation of Imine Reductases at 15 L Scale and Their Application in Asymmetric Piperazine Synthesis 156
3.6 Screening of Imine Reductases and Scale-Up of an Oxidative Deamination of an Amine for Ketone Synthesis 162
4 Transaminases 165
4.1 A Practical Dynamic Kinetic Transamination for the Asymmetric Synthesis of the CGRP Receptor Antagonist Ubrogepant 165
4.2 Asymmetric Biosynthesis of L-Phosphinothricin by Transaminase 168
4.3 Application of In Situ Product Crystallisation in the Amine Transaminase from Silicibacter pomeroyi-Catalysed Synthesis of (S)-1-(3-Methoxyphenyl)ethylamine 173
4.4 Enantioselective Synthesis of Industrially Relevant Amines Using an Immobilised omega-Transaminase 178
4.5 Amination of Sugars Using Transaminases 182
4.6 Converting Aldoses into Valuable omega-Amino Alcohols Using Amine Transaminases 187
5 Other Carbon-Nitrogen Bond-Forming Biotransformations 193
5.1 Biocatalytic N-Acylation of Anilines in Aqueous Media 193
5.2 Enantioselective Enzymatic Hydroaminations for the Production of Functionalised Aspartic Acids 196
5.3 Biocatalytic Asymmetric Aza-Michael Addition Reactions and Synthesis of L-Argininosuccinate by Argininosuccinate Lyase ARG4-Catalysed Aza-Michael Addition of L-Arginine to Fumarate 204
5.4 Convenient Approach to the Biosynthesis of C2,C6-Disubstituted Purine Nucleosides Using E. coli Purine Nucleoside Phosphorylase and Arsenolysis 211
5.5 Production of L- and D-Phenylalanine Analogues Using Tailored Phenylalanine Ammonia-Lyases 215
5.6 Asymmetric Reductive Amination of Ketones Catalysed by Amine Dehydrogenases 221
5.7 Utilisation of Adenylating Enzymes for the Formation of N-Acyl Amides 231
6 Carbon-Carbon Bond Formation or Cleavage 237
6.1 Improved Enzymatic Method for the Synthesis of (R)-Phenylacetyl Carbinol 237
6.2 Tertiary Alcohol Formation Catalysed by a Rhamnulose-1-Phosphate Aldolase : Dendroketose-1-Phosphate Synthesis 241
6.3 Easy and Robust Synthesis of Substituted L-Tryptophans with Tryptophan Synthase from Salmonella enterica 247
