Green Biocatalysis

Inbunden, Engelska, 2016

Av Ramesh N. Patel, Ramesh N. Patel, Ramesh N Patel

3 419 kr

Beställningsvara. Skickas inom 5-8 vardagar

Fri frakt för medlemmar vid köp för minst 249 kr.

Green Biocatalysis presents an exciting green technology that uses mild and safe processes with high regioselectivity and enantioselectivity. Bioprocesses are carried out under ambient temperature and atmospheric pressure in aqueous conditions that do not require any protection and deprotection steps to shorten the synthetic process, offering waste prevention and using renewable resources.Drawing on the knowledge of over 70 internationally renowned experts in the field of biotechnology, Green Biocatalysis discusses a variety of case studies with emphases on process R&D and scale-up of enzymatic processes to catalyze different types of reactions. Random and directed evolution under process conditions to generate novel highly stable and active enzymes is described at length. This book features: A comprehensive review of green bioprocesses and application of enzymes in preparation of key compounds for pharmaceutical, fine chemical, agrochemical, cosmetic, flavor, and fragrance industries using diverse enzymatic reactionsDiscussion of the development of efficient and stable novel biocatalysts under process conditions by random and directed evolution and their applications for the development of environmentally friendly, efficient, economical, and sustainable green processes to get desired products in high yields and enantiopurityThe most recent technological advances in enzymatic and microbial transformations and cuttingedge topics such as directed evolution by gene shuffling and enzyme engineering to improve biocatalystsWith over 3000 references and 800 figures, tables, equations, and drawings, Green Biocatalysis is an excellent resource for biochemists, organic chemists, medicinal chemists, chemical engineers, microbiologists, pharmaceutical chemists, and undergraduate and graduate students in the aforementioned disciplines.

Produktinformation

Utgivningsdatum2016-08-05
Mått224 x 282 x 46 mm
Vikt2 064 g
FormatInbunden
SpråkEngelska
Antal sidor800
FörlagJohn Wiley & Sons Inc
ISBN9781118822296

Tillhör följande kategorier

Ramesh N. Patel, Ph.D., has 44 years of experience in pharmaceutical and chemical industries. He obtained his Ph.D. in Biochemistry from the University of Texas, Austin, and completed an NIH and ACS Postdoctoral Research Fellowship in Biology from Yale University, New Haven. His professional experience includes working in Bristol-Myers Squibb and ExxonMobil Research and Engineering, where he has a record of achievements including over 175 original publications, 79 process patents, and over 113 invited/external presentations. Dr. Patel is the recipient of the 2004 Biotechnology Lifetime Achievement Award from the American Oil Chemists’ Society, the 2008 Biocat Industrial Research Award from the International Congress on Biocatalysis, and the 2012 Distinction of Academic Award from the International Society of World Academy of Biocatalysis and Agricultural Biotechnology. Currently he is working as a consultant in Biocatalysis and Biotechnology.

Preface xix About the Editor xxiiiContributors xxvChapter 1 Biocatalysis and Green Chemistry 1Roger A. Sheldon1.1 Introduction to Sustainable Development and Green Chemistry 11.2 Green Chemistry Metrics 21.3 Environmental Impact and Sustainability Metrics 41.4 Solvents 51.5 The Role of Catalysis 61.6 Biocatalysis and Green Chemistry 61.7 Examples of Green Biocatalytic Processes 81.8 Conclusions and Future Prospects 13Chapter 2 Enzymatic Synthesis of Chiral Amines using ω-Transaminases, Amine Oxidases, and the Berberine Bridge Enzyme 17Eduardo Busto, Robert C. Simon, Nina Richter, and Wolfgang Kroutil2.1 Introduction 172.2 Synthesis of Chiral Amines using ω]Transaminases 182.3 Amine Oxidases 342.4 Berberine Bridge Enzymes 502.5 Conclusions 52Chapter 3 Decarboxylation and Racemization of Unnatural Compounds using Artificial Enzymes Derived from Arylmalonate Decarboxylase 59Kenji Miyamoto3.1 Introduction 593.2 Discovery of a Bacterial α]Aryl]α]Methylmalonate Decarboxylase 613.3 Purification and Characterization of the Decarboxylase (Amdase) 613.4 Cloning of the Amdase Gene 623.5 Stereochemical Course of Amdase]Catalyzed Decarboxylation 623.6 Directed Evolution of Amdase to an Artificial Profen Racemase 633.7 Inversion of Enantioselectivity Dramatically Improves Catalytic Activity 653.8 Future Prospects 68Chapter 4 Green Processes for the Synthesis of Chiral Intermediates for the Development of Drugs 71Ramesh N. Patel4.1 Introduction 714.2 Saxagliptin: Enzymatic Synthesis of (S)]N]Boc]3]Hydroxyadamantylglycine 714.3 Sitagliptin: Enzymatic Synthesis of Chiral Amine 724.4 Vanlev: Enzymatic Synthesis of (S)]6]Hydroxynorleucine 734.5 Vanlev: Enzymatic Synthesis of Allysine Ethylene Acetal 744.6 Vanlev: Enzymatic Synthesis of Thiazepine 744.7 Tigemonam: Enzymatic Synthesis of (S)]β]Hydroxyvaline 764.8 Autoimmune Diseases: Enzymatic Synthesis of (S)]Neopentylglycine 764.9 Atazanavir: Enzymatic Synthesis of (S)]Tertiary Leucine 774.10 Thrombin Inhibitor (Inogatran): Synthesis of (R)]Cyclohexylalanine 784.11 Gamma Secretase Inhibitor: Enzymatic Synthesis of (R)]5,5,5]Trifluoronorvaline 794.12 NK1/NK2 Dual Antagonists: Enzymatic Desymmetrization of Diethyl 3][3′,4′]Dichlorophenyl] Glutarate 804.13 Pregabalin: Enzymatic Synthesis of Ethyl (S)]3]Cyano]5]Methylhexanoate 814.14 Chemokine Receptor Modulator: Enzymatic Synthesis of (1S,2R)]2](Methoxycarbonyl)-Cyclohex]4]ene]1]Carboxylic Acid 824.15 Enzymatic Synthesis of (3S,5R)]3](Aminomethyl)]5]Methyloctanoic Acid 824.16 Atorvastatin (Lipitor): Enzymatic Desymmetrization of 3]Hydroxyglutaronitrile 834.17 Anticancer Drugs: Enzymatic Synthesis of Taxane Side Chain 844.18 Antidiabetic and CNS Drugs: Enzymatic Hydrolysis of Dimethyl Bicyclo[2.2.1] Heptane]1,4]Dicarboxylate 854.19 Clopidogrel (Plavix): Enzymatic Preparation of 2]Chloromandelic Acid Esters 854.20 Antiviral Drug: Regioselective Enzymatic Acylation of Ribavirin 864.21 Anticholesterol Drug: Enzymatic Acylation of Alcohol 874.22 Saxagliptin: Enzymatic Synthesis of (5S)]4,5]Dihydro]1H]Pyrrole]1,5 Dicarboxylic Acid, 1](1,1]Dimethylethyl)]5]Ethyl Ester 884.23 Montelukast: Synthesis of Intermediate for LTD4 Antagonists 894.24 Atazanavir: Enzymatic Synthesis of (1S,2R)][3]Chloro]2]Hydroxy]1 (Phenylmethyl) Propyl]]Carbamic Acid,1,1]Dimethyl]Ethyl Ester 904.25 Atorvastatin: Enzymatic Synthesis of (R)]4]Cyano]3]Hydroxybutyrate 914.26 Antianxiety Drug: Enzymatic Synthesis of 6]Hydroxybuspirone 924.27 Protease Inhibitor: Enzymatic Synthesis of (R)]3](4]Fluorophenyl)]2]Hydroxy Propionic Acid 934.28 Dermatological and Anticancer Drugs: Enzymatic Synthesis of 2](R)]Hydroxy]2](1′,2′,3′, 4′]Tetrahydro]1′,1′,4′,4′]Tetramethyl]6′]Naphthalenyl) Acetate 944.29 Antipsychotic Drug: Enzymatic Reduction of 1](4]Fluorophenyl)4][4](5]Fluoro]2]Pyrimidinyl)1]Piperazinyl]]1]Butanone 954.30 Cholesterol]Lowering Agents: Enzymatic Synthesis of (3S,5R)]Dihydroxy]6](Benzyloxy) Hexanoic Acid, Ethyl Ester 954.31 Antimigraine Drugs: Enzymatic Synthesis of (R)]2]Amino]3](7]Methyl]1H]Indazol]5]yl) Propanoic Acid 964.32 Antidiabetic Drug (GLP]1 Mimics): Enzymatic Synthesis of (S)]Amino]3][3]{6](2]Methylphenyl)} Pyridyl]]Propionic Acid 974.33 Ephedrine: Synthesis of (R)]Phenylacetylcarbinol 984.34 Zanamivir: Enzymatic Synthesis of N]Acetylneuraminic Acid 994.35 Epivir: Enzymatic Deamination Process for the Synthesis of (2′R]cis)]2′]Deoxy]3]Thiacytidine 1004.36 HMG]CoA Reductase Inhibitors: Aldolase]Catalyzed Synthesis of Chiral Lactol 1014.37 Boceprevir: Oxidation of 6,6]Dimethyl]3]Azabicyclo[3.1.0]Hexane by Monoamine Oxidase 1024.38 Crixivan: Enzymatic Synthesis of Indandiols 1034.39 Potassium Channel Opener: Preparation of Chiral Epoxide and trans]Diol 1044.40 Epothilones (Anticancer Drugs): Epothilone B and Epothilone F 1054.41 β]Adrenergic Blocking Agents: Synthesis of Intermediates for Propranolol and Denopamine 1064.42 Conclusion 106Chapter 5 Dynamic Kinetic Resolution of Alcohols, Amines, and Amino Acids 115Jusuk Lee, Yoon Kyung Choi, Jaiwook Park, and Mahn]Joo Kim5.1 Introduction 1155.2 Dynamic Kinetic Resolution of Secondary Alcohols 1195.3 Dynamic Kinetic Resolution of Amines and Amino Acids 1335.4 Applications of Dynamic Kinetic Resolution 1395.5 Summary 145Appendix: List of Abbreviations 145Chapter 6 Recent Developments in Flavin-Based Catalysis: Enzymatic Sulfoxidation 149Patricia B. Brondani, Marco W. Fraaije, and Gonzalo de Gonzalo6.1 Introduction 1496.2 Enzymatic Sulfoxidation Catalyzed by Flavoprotein Oxidases 1506.3 Use of Flavoprotein Monooxygenases for the Synthesis of Chiral Sulfoxides 1516.4 Asymmetric Sulfoxidation using Flavins as Catalysts 1606.5 Summary and Outlook 162Chapter 7 Development of Chemoenzymatic Processes: An Industrial Perspective 165Rajesh Kumar, Carlos Martinez, Van Martin, and John Wong7.1 Introduction 1657.2 Synthetic Route Design and Integration of Biocatalysis 1667.3 Screening and Biocatalyst Selection 1697.4 Chemoenzymatic Process Development 1697.5 Conclusions 176Chapter 8 Epoxide Hydrolases and their Application in Organic Synthesis 179Alain Archelas, Gilles Iacazio, and Michael Kotik8.1 Introduction 1798.2 Sources and Reaction Mechanism of EHs 1818.3 Directed Evolution and Genetic Engineering of EHs 1838.4 Immobilized EHs and Reactions in Nonaqueous Media 1868.5 Monofunctional Epoxides as Chiral Building Blocks for the Synthesis of Biologically Active Compounds 1888.6 Preparation of Valuable Chiral Building Blocks for the Synthesis of Biologically Active Compounds Starting from Bifunctional Epoxides 2048.7 Application to Natural Product Synthesis 2108.8 Bienzymatic Process Implying One Epoxide Hydrolase 2168.9 Conclusions 219Chapter 9 Enantioselective Acylation of Alcohol and Amine Reactions in Organic Synthesis 231Vicente Gotor]Fernández and Vicente Gotor9.1 Introduction 2319.2 Enantioselective Acylation of Alcohols 2349.3 Acylation of Amines 2489.4 Conclusions 260Chapter 10 Recent Advances in Enzyme-Catalyzed Aldol Addition Reactions 267Pere Clapés10.1 Introduction 26710.2 Pyruvate-Dependent Aldolases 26910.3 Dihydroxyacetone Phosphate (DHAP)-Dependent Aldolases, d-Fructose-6-Phosphate Aldolase (FSA) and Transaldolases 27610.4 Threonine Aldolases 28710.5 Aldol Type Reactions Catalyzed by Non]Aldolases 29310.6 Computational De Novo Enzyme Design 29410.7 Conclusions and Perspectives 295Chapter 11 Enzymatic Asymmetric Reduction of Carbonyl Compounds 307Tomoko Matsuda, Rio Yamanaka, and Kaoru Nakamura11.1 Introduction 30711.2 Mechanisms 30711.3 Preparation of Biocatalysts 30911.4 Solvent Engineering 31611.5 Examples for Biocatalytic Asymmetric Reductions 31711.6 Conclusions 325Chapter 12 Nitrile]Converting Enzymes and their Synthetic Applications 331Ludmila Martínková12.1 Introduction 33112.2 Screening Methodology 33212.3 Nitrilases 33312.4 Nitrile Hydratases 34012.5 Conclusions 343Acknowledgements 343Chapter 13 Biocatalytic Epoxidation for Green Synthesis 351Hui Lin, Meng]Yu Xu, Yan Liu, and Zhong]Liu Wu13.1 Introduction 35113.2 Enzymes for Asymmetric Epoxidation 35213.3 Application of Bioepoxidation in Organic Synthesis 35413.4 Protein Engineering for Biocatalytic Epoxidation Reaction 36213.5 Conclusions and Outlook 367Acknowledgments 368Chapter 14 Dynamic Kinetic Resolution via Hydrolase–Metal Combo Catalysis 373Pilar Hoyos, Vittorio Pace, María J. Hernáiz, and Andrés R. Alcántara14.1 Introduction 37314.2 DKR of Secondary Alcohols 37414.3 DKR of Amines 38614.4 Conclusion 391Chapter 15 Discovery and Engineering of Enzymes for Peptide Synthesis and Activation 397Ana Toplak, Muhammad I. Arif, Bian Wu, and Dick B. Janssen15.1 Introduction 39715.2 Classification of Enzymes for Peptide Coupling 39915.3 Serine and Cysteine Proteases for Peptide Synthesis 40215.4 Protease Discovery 40915.5 Proteases Engineered for Improved Synthesis 41015.6 Enzymes for Peptide Terminal Modification 41215.7 Conclusions 415Chapter 16 Biocatalysis for Drug Discovery and Development 421Youyun Liang, Mingzi M. Zhang, Ee Lui Ang, and Huimin Zhao16.1 Introduction 42116.2 Single Enzymatic Reactions 42316.3 Multienzyme Biocatalytic Reactions 43716.4 Future Perspective: Biocatalysts for the Pharmaceutical Industry 44516.5 Conclusion 448Chapter 17 Application of Aromatic Hydrocarbon Dioxygenases 457Watumesa A. Tan and Rebecca E. Parales17.1 Introduction 45717.2 Challenges in Aromatic Hydrocarbon Dioxygenase Applications 45717.3 Protein Engineering to Improve Enzymatic Activity and Alter Substrate Specificity 45917.4 Protein Engineering for the Production of Specific Chemicals 46417.5 Strain Modification for the Development of New Biodegradation Pathways 46717.6 Phytoremediation: The Expression of Bacterial Dioxygenases in Plant Systems for Bioremediation Purposes 46817.7 Concluding Remarks 469Acknowledgments 469Chapter 18 Ene]reductases and their Applications 473Tanja Knaus, Helen S. Toogood, and Nigel S. Scrutton18.1 Introduction 47318.2 Substrate Classes and Industrial Applications 47418.3 Multienzyme Reactions 47818.4 Alternative Hydride Sources 47918.5 Improvements of Productivity, Stereoselectivity, and/or Conversion 482Chapter 19 Recent Developments in Aminopeptidases, Racemases, and Oxidases 489Yasuhisa Asano, Seiji Okazaki, and Kazuyuki Yasukawa19.1 Aminopeptidase 48919.2 Racemase 49219.3 Amino Acid Oxidase 495Chapter 20 Biocatalytic Cascades for API Synthesis 503John M. Woodley20.1 Introduction 50320.2 Multienzymatic Biocatalysis 50420.3 Process Aspects for Multistep Biocatalysis 50620.4 Process Development 51120.5 Biocatalytic Cascade Examples 51220.6 Future Outlook 515Chapter 21 Yeast-Mediated Stereoselective Synthesis 519René Csuk21.1 Introduction 51921.2 Reductions of Aldehydes and Ketones 52121.3 Reduction of Thiocarbonyls or Sulfur]Containing Compounds 52421.4 Reduction of Functionalized Carbonyl and Dicarbonyl Compounds 52421.5 Reduction of Keto Esters 52721.6 Hydrolysis of Esters 52921.7 Immobilized Baker’s Yeast 53021.8 Whole]Cell Biocatalysis in Ionic Liquids and Deep Eutectic Solvents 53121.9 C„ŸC Bond]Forming and Breaking Reactions 53221.10 Miscellaneous Reactions 53321.11 Conclusions 534Chapter 22 Biocatalytic Introduction of Chiral Hydroxy Groups using Oxygenases and Hydratases 545Jun Ogawa, Makoto Hibi, and Shigenobu Kishino22.1 Introduction 54522.2 Regio] and Stereoselective Hydroxylation of Propylbenzene and 3]Chlorostyrene by Cytochrome P450 BM]3 and its Mutant 54622.3 Regio] and Stereoselective Hydroxylation of Aliphatic Amino Acids by Fe(Ii)/α]Ketoglutarate]Dependent Dioxygenases 54722.4 Regio] and Stereoselective Hydration of Unsaturated Fatty Acids by a Novel Fatty Acid Hydratase 55122.5 Conclusion 553Acknowledgment 553Chapter 23 Asymmetric Synthesis with Recombinant Whole]Cell Catalyst 557Harald Gröger, Werner Hummel, and Severin Wedde23.1 Introduction 55723.2 The Design/Construction of Whole]Cell Catalysts 55823.3 Biotransformations with Whole]Cell Catalysts 56123.4 Conclusion 581Chapter 24 Lipases and Esterases as User-Friendly Biocatalysts in Natural Product Synthesis 587Kenji Mori24.1 Introduction 58724.2 Desymmetrization of Prochiral or meso]Diols and Diacetates 58724.3 Kinetic Resolution of Racemic Alcohols 59224.4 Preparation of Enantiopure Intermediate(s) from a Mixture of Stereoisomers 59924.5 Conclusion 601Acknowledgments 601Chapter 25 Hydroxynitrile Lyases for Biocatalytic Synthesis of Chiral Cyanohydrins 603Romana Wiedner, Helmut Schwab, and Kerstin Steiner25.1 Introduction 60325.2 Discovery of Hydroxynitrile Lyases: Bioprospecting 60425.3 Applications of Hydroxynitrile Lyases 60925.4 Structural and Mechanistic Aspects 61125.5 Engineering of Hydroxynitrile Lyases 61225.6 Reaction Engineering and Reaction Systems 62025.7 Conclusion 623Acknowledgment 623Chapter 26 Biocatalysis: Nitrilases in Organic Synthesis 629Jin]Song Gong, Jin]Song Shi, and Zheng]Hong Xu26.1 Introduction 62926.2 Nitrilase Discovery 63026.3 Nitrilase Improvement 63126.4 Applications in Organic Synthesis 63526.5 Conclusions and Future Prospects 638Acknowledgments 639Chapter 27 Biotechnology for the Production of Chemicals, Intermediates, and Pharmaceutical Ingredients 643Hans]Peter Meyer27.1 Introduction 64327.2 Value Chains and Markets 64527.3 The Toolbox 66127.4 Sustainability, Green Premium Pricing, and Subsidies 66527.5 Regulatory Aspects and Public Perception 66727.6 Innovation (Not Only in the Laboratory!) 66927.7 Conclusions 670Acknowledgments 671Chapter 28 Microbial Transformations of Pentacyclic Triterpenes 675Robert Azerad28.1 Introduction 67528.2 Typical Biotransformations in the Lupane Family 67728.3 Typical Biotransformations in the Oleane Family 68028.4 Typical Biotransformations in the Ursane Family 69228.5 Microbial Transformations of Other Pts 70428.6 Glycosylations and Deglycosylations 70428.7 Conclusion and Perspectives 710Chapter 29 Transaminases and their Applications 715Sarah-Marie Dold, Christoph Syldatk, and Jens Rudat29.1 Introduction 71529.2 General Properties of Transaminases 71529.3 Synthesis Strategies with Transaminases 71929.4 Approaches to Optimize the Transaminase]Catalyzed Reactions 73529.5 Conclusion 743Index 747