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Organic Synthesis Using Biocatalysis

1st Edition - September 2, 2015

Editors: Animesh Goswami, Jon D. Stewart

Hardback ISBN:

9 7 8 - 0 - 1 2 - 4 1 1 5 1 8 - 7

eBook ISBN:

9 7 8 - 0 - 1 2 - 4 1 1 5 4 2 - 2

Organic Synthesis Using Biocatalysis provides a concise background on the application of biocatalysis for the synthesis of organic compounds, including the important biocatalytic… Read more

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Organic Synthesis Using Biocatalysis provides a concise background on the application of biocatalysis for the synthesis of organic compounds, including the important biocatalytic reactions and application of biocatalysis for the synthesis of organic compounds in pharmaceutical and non-pharmaceutical areas.

The book provides recipes for carrying out various biocatalytic reactions, helping both newcomers and non-experts use these methodologies. It is written by experts in their fields, and provides both a current status and future prospects of biocatalysis in the synthesis of organic molecules.

List of Contributors
Chapter 1: Introduction, Types of Reactions, and Sources of Biocatalysts
- Abstract
- 1. Introduction
- 2. Definition of biocatalysis
- 3. Scope of this book
- 4. Key benefits of employing enzymes in synthesis
- 5. Mechanism and kinetics of enzyme-catalyzed reactions
- 6. Types of enzyme-catalyzed reactions commonly used in biocatalysis
- 7. Sources of biocatalysts
- 8. Types of enzyme preparation
- 9. Availability of enzymes for biocatalysis
Chapter 2: Practical and Engineering Aspects of Running Enzyme Reactions
- Abstract
- 1. Introduction
- 2. Availability of an efficient enzyme as a catalyst: screening and protein engineering
- 3. The role of cofactors and practical concepts for their in situ regeneration
- 4. Enzyme formulation
- 5. Immobilization and reuse of catalysts
- 6. Reagent/Substrate engineering
- 7. Reaction media engineering
- 8. Reaction engineering: batch versus continuously running processes
- 9. Summary
Chapter 3: Biocatalysis in Organic Solvents, Supercritical Fluids and Ionic Liquids
- Abstract
- 1. Introduction
- 2. Key attributes of reactions in nonaqueous solvents
- 3. Kinds of nonaqueous solvents used for biocatalysis
- 4. Solubility of enzymes, substrates, and products in nonaqueous solvents
- 5. Stability of enzymes in nonaqueous solvents
- 6. Selection of nonaqueous solvents for a desired reaction
- 7. Examples of reactions in organic solvents
- 8. Examples of reactions in aqueous – organic biphasic systems
- 9. Examples of reactions in supercritical fluids
- 10. Examples of reactions in aqueous – supercritical fluids biphasic systems
- 11. Examples of reactions in ionic liquids
- 12. Examples of reactions in aqueous – ionic liquids biphasic systems
- 13. Examples of reactions in ionic liquids – supercritical fluids biphasic systems
- 14. Conclusions
Chapter 4: Enzyme Immobilization for Organic Synthesis
- Abstract
- 1. Introduction
- 2. Immobilization techniques
- 3. Specific examples of immobilized biocatalysts
Chapter 5: Hydrolysis and Formation of Carboxylic Acid and Alcohol Derivatives
- Abstract
- 1. Introduction – hydrolases commonly used in organic synthesis
- 2. Choosing a hydrolase – substrate specificity and enantioselectivity
- 3. Enantiopure compounds: resolutions, desymmetrizations, and dynamic kinetic resolutions
- 4. Choosing reaction conditions – water or organic solvent
- 5. Example reactions
Chapter 6: Modern Biocatalytic Ketone Reduction
- Abstract
- 1. Introduction
- 2. Mechanism of enzymatic ketone reduction
- 3. Recent bioreduction examples
- 4. Immobilization of CRED enzymes and membrane applications
- 5. Ionic liquids and CRED enzymes
- 6. Future outlook
- 7. Practical examples
- 8. Conclusions
Chapter 7: Organic Synthesis with Amino Acid Dehydrogenases, Transaminases, Amine Oxidases, and Amine Dehydrogenases
- Abstract
- 1. Introduction
- 2. Amino acid dehydrogenases
- 3. Transaminases
- 4. Amine oxidase
- 5. Amine dehydrogenases
- Acknowledgment
Chapter 8: Biocatalysis for Organic Chemists: Hydroxylations
- Abstract
- 1. Introduction
- 2. Cytochrome P450s
- 3. Examples of P450-catalysed biotransformations
- 4. Flavin-dependent hydroxylases
- 5. 2-Oxoglutarate dependent hydroxylases
- 6. Conclusions
Chapter 9: Miscellaneous Key Non-C―C Bond Forming Enzyme Reactions
- Abstract
- 1. Nitrile hydratases
- 2. Nitrilases
- 3. Hydantoinases and carbamoylases
- 4. Epoxide hydrolase for epoxide and diol formation
- 5. Dehalogenase
- 6. Enoate reductases
- 7. Baeyer–Villiger monooxygenases
- 8. Dihydroxylation of aromatic compounds
- 9. Experimental procedures
Chapter 10: Enzymatic C―C Bond Formation
- Abstract
- 1. Hydroxynitrile lyases
- 2. Carbon–carbon bond formation using thiamin diphosphate (ThDP)-dependent carboligases
- 3. Enzymatic aldol additions
Chapter 11: Applications of Biocatalysis for Pharmaceuticals and Chemicals
- Abstract
- 1. Introduction
- 2. Enzymatic enantioselective hydrolysis and desymmetrization
- 3. Enzymatic esterification, transesterification, and amidation
- 4. Enzymatic acylation
- 5. Ketoreductases and chiral alcohols
- 6. Enzymatic transamination reactions
- 7. Enzymatic reductive amination
- 8. Enzymatic hydroxylation
- 9. Application of biocatalysis in basic and specialty Chemicals
- 10. Conclusions
- Acknowledgments
Chapter 12: Future of Biocatalysis in the Synthesis of Organic Compounds
- Abstract
Subject Index

Animesh Goswami

Dr. Animesh Goswami has more than 25 years of industrial experience and is an expert in the industrial application of biocatalysis for the synthesis of organic compounds. He joined Bristol-Myers Squibb in 1998 and is currently a research fellow leading the Biocatalysis group of Chemical Development department. Before joining Bristol-Myers Squibb, he worked in research and development of Rhone-Poulenc in USA for eleven years. He is author/co-author of forty five publications and fifteen patents and patent applications. He has published extensively and has given numerous invited lecturers in national and international meetings in the area of biocatalysis. Dr. Goswami earned his Ph.D from the University of North Bengal in India and has conducted post-doctoral studies at Arizona State University and University of Iowa in USA. He is a member of the American Chemical Society and the Society for Industrial Microbiology and Biotechnology.

Affiliations and expertise

Chemical Development, Bristol-Myers Squibb, New Brunswick, NJ, USA

Jon D. Stewart

Dr. Jon D. Stewart has led his academic research group at the University of Florida since joining the department in 1994 as an Assistant Professor. He was promoted to Professor of Chemistry in 2006 and also has affiliate appointments in the Departments of Biochemistry & Molecular Biology and Biomedical Engineering. His research has included a number of topics in biocatalysis including Baeyer-Villiger monooxygenases, nicotinamide-dependent carbonyl reductases with a current emphasis on alkene reductases. He has authored or co-authored 100 research publications and has given numerous invited lectures at meetings and companies. He has served as an editor for the Journal of Molecular Catalysis B: Enzymatic since 2003. Dr. Stewart earned B.S. and M.S. degrees from Bucknell University, his Ph.D. from Cornell University and was a Helen Hay Whitney Postdoctoral Fellow at Penn State University.

Affiliations and expertise

University of Florida, Gainesville, FL, USA