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Index
Cover
Title
Copyright
Contents
Preface
Part I Context and Challenges for Industrial Biocatalysis
Chapter 1 An Appreciation of Biocatalysis in the Swiss Manufacturing Environment
1.1 Introduction
1.1.1 Biocatalysis in the Swiss Manufacturing Environment
1.1.2 Current Status
1.1.3 Patent Analysis
1.2 Selected Enzyme Classes Used in the Swiss Manufacturing Environment
1.2.1 Oxidoreductases EC1
1.2.2 Transferases EC2
1.3 Challenges
1.3.1 Regulation
1.3.2 Development Time
1.3.3 Technological Lock-in
1.3.4 Public Perception
1.3.5 Education
1.4 Opportunities
1.4.1 Starting Materials
1.4.2 Sustainability and Greenness
1.4.3 Swiss Industrial Biocatalysis Consortium
1.4.4 New Business Ideas
1.5 Future Directions
Acknowledgements
References
Chapter 2 Biocatalysis – A Greener Alternative in Synthetic Chemistry
2.1 Introduction
2.2 Motivation for Industry to Use/Research on Biocatalysis
2.3 Challenges Faced by Biocatalysis in Industry
2.4 Prospects,
2.5 Overview of Current Enzyme-based Processes Implemented/In-progress at Industrial, Commercial Scale
2.6 Our Experience in Some Chemoenzymatic Projects
2.6.1 Protease-mediated Synthesis of Valganciclovir Intermediate
2.6.2 Chemoenzymatic Synthesis of Optically Pure Rivastigmine Intermediate Using ADH from Baker’s Yeast and KRED,
2.6.3 Preparation of Deoxynojirimycin, Key Intermediate of an Anti-diabetic Drug
2.7 Potential Safety Aspects
2.8 Conclusions
Abbreviations
Glossary
References
Chapter 3 Biocatalytic Synthesis of Small Molecules – Past, Present and Future
3.1 Introduction
3.2 Biocatalytic Conversions of Racemates
3.2.1 Biocatalytic Resolution of Racemates
3.2.2 Biocatalytic Deracemizations
3.3 Biocatalytic Desymmetrizations
3.4 Biocatalytic Asymmetric Oxidations and Reductions
3.4.1 Biocatalytic Asymmetric Oxidations
3.4.2 Biocatalytic Asymmetric Reductions
3.5 Biocatalytic Asymmetric Hydrolysis and Acylation Reactions
3.5.1 Biocatalytic Asymmetric Hydrolysis Reactions
3.5.2 Biocatalytic Asymmetric Acylation Reactions
3.6 Biocatalytic Asymmetric Transfer Reactions
3.7 Biocatalytic Asymmetric Addition and Elimination Reactions
3.8 Summary and Outlook
References
Chapter 4 EntreChem: Building a Sustainable Business Case in Biotechnology: From Biocatalysis to Synthetic Biology
4.1 Introduction
4.2 Biocatalysis
4.2.1 Enantiopure Chiral Building Blocks
4.2.2 Cascade Processes Taking Advantage of Biocatalysis
4.3 Drug Development
4.3.1 Natural Products in Drug Discovery
4.3.2 EntreChem’s Approach to Natural Products Drug Discovery
4.3.3 Aureolic Acids: The Quest for Clinically Viable “Mithralogs”
4.3.4 Collismycin Analogs as Immunosuppressive and Neuroprotective Drugs
4.3.5 Glycosylated Indolocarbazoles as Potent and Selective Kinase Inhibitors
4.4 Business Models in Biocatalysis and Natural Products Drug Discovery
References
Part II Biocatalysis: from Pharmaceuticals to Bulk Chemistry
Chapter 5 Bristol-Myers Squibb: Preparation of Chiral Intermediates for the Development of Drugs and APIs
5.1 Introduction
5.2 Anti-Alzheimer's Drug. Enzymatic Preparation of (R)-5,5,5-Trifluoronorvaline
5.3 Cholesterol Lowering Agents
5.3.1 Enantioselective Enzymatic Acylation of Racemic Alcohol
5.3.2 Enzymatic Synthesis of (3S,5R)-Dihydroxy-6-(benzyloxy)hexanoic Acid, Ethyl Ester
5.4 Calcitonin Gene-related Peptide Receptors Antagonists (Migraine Treatment): Enzymatic Preparation of (R)-2-Amino-3-(7-methyl-1H-indazol-5-yl)propanoic Acid
5.5 Antidiabetic Drugs
5.5.1 Saxagliptin: Enzymatic Synthesis of (S)-N-Boc-3-hydroxyadamantylglycine
5.5.2 Saxagliptin: Enzymatic Synthesis of N-Cbz-4,5-dehydro-L-prolineamide and N-Boc-4,5-dehydro-L-prolineamide
5.5.3 Saxagliptin: Enzymatic Ammonolysis of (5S)-4,5-Dihydro-1H-pyrrole-1,5-dicarboxylic Acid, 1-(1,1-Dimethylethyl)-5-ethyl Ester
5.5.4 GLP-1 Receptor Agonists: Enzymatic Preparation of (S)-Amino-3-[3-{6-(2-methylphenyl)}pyridyl]-propionic Acid
5.6 Antihypertensive Drugs
5.6.1 Enzymatic Synthesis of (S)-6-Hydroxynorleucine
5.6.2 Vanlev: Enzymatic Synthesis of Allysine Ethylene Acetal
5.6.3 Vanlev: Enzymatic Synthesis of Thiazepine
5.6.4 Captopril: Enzymatic Preparation of (S)-3-Benzoylthio-2-methylpropanoic Acid
5.7 Antiviral Drugs. Case Study: Atazanavir
5.7.1 Atazanavir: Enzymatic Synthesis of (S)-Tertiary-leucine
5.7.2 Atazanavir: Enzymatic Preparation of (1S,2R)-[3-Chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic Acid, 1,1-Dimethyl-ethyl Ester
5.8 Antianxiety Drug. Buspirones: Enzymatic Preparation of 6-Hydroxybuspirone
5.9 Antiviral Drugs. Hepatitis B Viral (HBV) Inhibitor: Enzymatic Asymmetric Hydrolysis and Acetylation
5.10 Chemokine Receptor Modulators: Enzymatic Desymmetrization of Dimethyl Ester
5.11 Anticancer Drugs
5.11.1 Paclitaxel Semisynthetic Process
5.11.2 Water-soluble Taxane Derivatives
5.11.3 Epothilones: Epothilone B and Epothilone F
5.11.4 IGF-1 Receptor Inhibitor: Enzymatic Preparation of (S)-2-Chloro-1-(3-chlorophenyl)ethanol
5.11.5 Retinoic Acid Receptor Agonist: Enzymatic Preparation of 2-(R)-Hydroxy-2-(1′,2′,3′,4′-tetrahydro-1′,1′,4′,4′-tetramethyl-6′-naphthalenyl)acetate
5.12 Microbial Hydroxylation of Mutilin and Pleuromutilin
5.13 Conclusions
Acknowledgements
References
Chapter 6 Johnson Matthey: A Technology Provider Perspective to Biocatalysis in the Fine Chemicals Industry
6.1 Introduction
6.2 Commercial Considerations
6.2.1 Technology Value
6.2.2 Manufacturing
6.2.3 Market Analysis
6.2.4 Catalyst Portfolio
6.3 Technical Considerations
6.3.1 Enzyme Recruitment
6.3.2 Enzyme Engineering
6.3.3 Process Improvement
6.4 Conclusions
Acknowledgements
References
Chapter 7 EnzymeWorks: Recent Advances in Enzyme Engineering for Chemical Synthesis
7.1 Introduction to EnzymeWorks
7.1.1 Current Status of Biocatalyst Development
7.2 Biocatalysis in the Food and Beverage Industry
7.2.1 Introduction of Stevia Development
7.2.2 Plant Family 1 UDP-glycosyltransferase Applications
7.2.3 Chemoenzymatic Synthesis of Rebaudioside M
7.2.4 Enzyme Immobilization and Whole Cell Biosynthesis Development
7.2.5 Future Perspectives on Biocatalysis in the Food and Beverage Industry
7.3 Ketoreductase (KRED) Applications
7.3.1 Ibrutinib Development
7.3.2 Future Perspectives on Ketoreductase (KRED) Biocatalysis
7.4 Biocatalysis in the Antibiotic Industry
7.4.1 Introduction to Cephalosporin C Acylase (CCA)
7.4.2 Gene Expression, Structure and Catalytic Mechanism of Acylases
7.4.3 Recent Advances in Cephalosporin C Acylase (CCA) Development
7.4.4 Future Perspectives on Acylase Biocatalysis
7.4.5 Introduction to Deacetoxycephalosporin C Synthase
7.4.6 Deacetoxycephalosporin C Synthase Structure and Mechanism
7.4.7 Recent Advances in Deacetoxycephalosporin C Synthase Development
7.4.8 Future Perspectives of Antibiotic Biocatalysis
7.5 Future Perspectives of Biocatalyst Development
References
Chapter 8 Almac: An Industrial Perspective of Ene Reductase (ERED) Biocatalysis
8.1 Introduction
8.1.1 Almac Group
8.1.2 Biocatalysis at Almac
8.1.3 The Rise of Biocatalysis
8.2 Introduction to Alkene Reduction
8.3 An Introduction to Ene Reductases and How They Work
8.4 Examples of Ene Reductase Reactions Reported in the Literature
8.4.1 Ene Reductases as Part of a Reaction Sequence
8.4.2 Ene Reductases and Solvents
8.4.3 Challenges of Co-factor Recycle
8.4.4 Avoiding the Use of Nicotinamide Co-factors
8.4.5 Impact of Synthetic Biology
8.4.6 Ene Reductases in Reverse: Oxidation
8.4.7 Thermophilic Ene-reductases
8.4.8 Alternative Screening Methods
8.5 Example of Utilisation of an ERED at Industrial Scale
8.6 Transition of Ene Reductases to Mainstream Biocatalytic Use
8.7 Conclusions
Acknowledgements
References
Chapter 9 GSK: Biocatalyst Discovery and Optimisation
9.1 Introduction
9.2 Biocatalyst Discovery
9.2.1 Design of Enzyme Panels
9.2.2 Imine Reductase Panel – Importance and Applicability
9.3 Biocatalyst Optimisation
9.3.1 Nelarabine Case Study
9.4 Conclusions
Acknowledgements
References
Chapter 10 PETROBRAS: Efforts on Biocatalysis for Fuels and Chemicals Production
10.1 PETROBRAS Overview
10.2 Hydrolysis of Lignocellulosic and Starchy Biomass
10.3 Synthesis of Solvents
10.3.1 Glycerol Carbonate
10.3.2 Butyl Acetate
10.4 Synthesis and Degradation of Polymers
10.4.1 Synthesis of Polyesters
10.4.2 Depolymerization of Poly(ethylene terephthalate)
10.5 Synthesis of Biolubricants
10.6 Synthesis of Biodiesel
10.7 Concluding Remarks
References
Chapter 11 MetGen: Value from Wood – Enzymatic Solutions
11.1 Introduction
11.1.1 METGEN – Masters of Enzyme Technology and Genetic Engineering
11.1.2 Biocatalysis of Wood – Motivation and Challenges
11.2 Enzymes in Pulp and Paper
11.2.1 Enzymes in Pulp & Paper Industry Sector – Business Aspect
11.2.2 Major Enzyme Components for Wood Applications
11.2.3 Enzyme Development – from Laboratory to Industry
11.2.4 MetZyme® LIGNO™
11.2.5 MetZyme® BRILA™
11.2.6 Concluding Remarks on Enzymes in Pulp and Paper
11.3 Biorefinery Enzymes
11.3.1 Renewable Chemical Industry Segment – Business Aspect
11.3.2 Wood Biorefinery Concept
11.3.3 Biomass Hydrolysis – Chemicals and Enzymes
11.3.4 Biomass Is Not Oil; It Is More Like Soup of the Day
11.3.5 Beyond Sugars
11.3.6 Biorefinery Enzymes – Concluding Remarks
11.3.7 Wood in Pulp and Paper and Biorefinery – Common Problems or Window for Opportunity?
Abbreviations
References
Part III Biocatalyst Optimization with Industrial Perspectives
Chapter 12 LentiKat’s: Industrial Biotechnology, Experiences and Visions
12.1 Introduction
12.2 Lentikats Biotechnology
12.2.1 Potential of Lentikats Biotechnology
12.2.2 Properties of Lentikats Biotechnology
12.2.3 Production of Lentikats Biocatalyst
12.3 Experiences in Wastewater Treatment
12.3.1 Municipal Wastewater Treatment
12.3.2 Industrial Wastewater Treatment
12.3.3 Special Applications
12.3.4 Advantages of Lentikats Biotechnology in Wastewater Treatment
12.3.5 Product Lines
12.3.6 Wastewater Treatment Applications
12.4 Experiences in the Pharmaceutical & Food Industry
12.4.1 Food Technology Industry
12.4.2 Pharmaceutical Industry
12.4.3 Bio-based Chemicals Industry
12.4.4 Advantages of Lentikats Biotechnology in the Pharmaceutical & Food Industry
12.4.5 Application Examples in the Pharmaceutical & Food Industry
12.4.6 Pharmaceutical & Food Applications
12.5 Vision
References
Chapter 13 EziG: A Universal Platform for Enzyme Immobilisation
13.1 Introduction
13.2 A General Methodology for Enzyme Reuse
13.2.1 The Potential of Biocatalysis by Far Exceeds Its Current Exploitation
13.2.2 Unlocking the Potential of Enzymes
13.2.3 Immobilised Enzymes for the Pharmaceutical Industry
13.2.4 The Reusable Enzyme Utopia – Enzymes Anchored in Space
13.2.5 The EziG Technology
13.2.6 Standardised Procedure for Immobilisation
13.2.7 Lower Cost Materials versus High Performance
13.3 Case Studies
13.3.1 In-reactor Enzyme Immobilisation
13.3.2 Two-phase System in Flow for in situ Product Removal
13.3.3 Candida antarctica Lipase B (CalB)
13.3.4 Co-immobilisation for Cascade Reactions
13.4 Prospects
13.4.1 Stability versus Activity – Replacing Low Cost Catalysts
13.4.2 Biocatalysis in Flow – Towards Manufacturing Processes in Continuous Mode
13.5 Conclusions
Acknowledgements
References
Chapter 14 Cross-linked Enzyme Aggregates (CLEAs): From Concept to Industrial Biocatalyst
14.1 Introduction: Biocatalysis is Green and Sustainable
14.2 Immobilisation of Enzymes
14.3 The CLEA Technology
14.3.1 The Concept
14.3.2 Preparation of CLEAs
14.3.3 Physical Properties of CLEAs
14.3.4 Advantages and Limitations of CLEAs
14.3.5 Reactor Design
14.4 Scope of the CLEA Technology
14.4.1 Hydrolase CLEAs
14.4.2 Oxidoreductase and Lyase CLEAs
14.5 Multi- and Combi-CLEAs
14.6 Magnetic CLEAs: The New Frontier
14.7 Applications of CLEAs, Combi-CLEAs and mCLEAs
14.7.1 1G and 2G Biofuels Production
14.7.2 Food and Beverages Processing
14.7.3 Synthesis of Semi-synthetic Penicillin and Cephalosporin Antibiotics
14.7.4 Removal of Dyes, Pharma Residues and Endocrine Disruptors from Waste Water
14.7.5 Other Potential Applications
14.8 Conclusions and Future Prospects
References
Chapter 15 SynBiocat: Protein Purification, Immobilization and Continuous-flow Processes
15.1 Introduction
15.2 SynBiocat – From Protein Purification to Continuous-flow Processes
15.2.1 Enzyme Production and Purification
15.2.2 Enzyme Immobilization
15.2.3 Desktop Bioreactor Applications
15.3 Conclusion
List of Abbreviations
Acknowledgements
References
Part IV Emerging Industrial Biocatalysis
Chapter 16 Microvi: MicroNiche Engineering™ for Biocatalysis in the Water and Chemical Industries
16.1 Introduction to Microvi
16.2 Microvi’s MicroNiche Engineering™ Platform
16.3 Case Study: MicroNiche Biocatalysts for Water Purification
16.4 Producing Case Study: MicroNiche Biocatalysts for Biobased Chemicals
16.5 Conclusions
References
Chapter 17 Nofima: Peptide Recovery and Commercialization by Enzymatic Hydrolysis of Marine Biomass
17.1 Nofima: The Company
17.2 Hydrolysis of Marine Biomass
17.2.1 Chemical Hydrolysis of Marine Biomass
17.2.2 Enzymatic Hydrolysis of Marine Biomass
17.3 Enzymes Used for Bioconversion
17.4 Quality and Classification of Marine Biomass
17.5 Functional Properties and Bioactivities of Hydrolyzed Marine Biomass
17.6 Commercialization of Products from Marine Biomass
17.7 Conclusions
17.8 Case Examples
17.8.1 Marealis – Producing a Nutraceutical from Shrimp Peels
17.8.2 Polybait AS – Producing Fishing Bait from Fisheries By-products
References
Chapter 18 CO2 Solutions: A Biomimetic Approach to Mitigate CO2 Emissions – The Use of Carbonic Anhydrase in an “Industrial Lung”
18.1 Introduction
18.2 Conventional Post-combustion CO2 Capture Technologies
18.3 CSI’ Technology: An Industrial Lung
18.4 Selection and Development of a Robust CA
18.4.1 Elevated Ionic Strength
18.4.2 High pH
18.4.3 Temperatures Above 60 °C
18.4.4 Effect of High Surface Volume Ratio
18.4.5 Effect of High Shear Stress
18.4.6 Effect of Contaminants
18.4.7 Effect of Solid–Liquid Interface
18.4.8 Carbonic Anhydrase Development
18.5 Technology Validation/Demonstration at Pilot Scale
18.6 Conclusions
Acknowledgements
References
Subject Index
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