Green Biocatalysis (eBook, PDF)

Redaktion: Patel, Ramesh N.

• Format: PDF

Produktbeschreibung

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 reactions * Discussion 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 enantiopurity * The most recent technological advances in enzymatic and microbial transformations and cuttingedge topics such as directed evolution by gene shuffling and enzyme engineering to improve biocatalysts With 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.

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Produktdetails

• Verlag: Jossey-Bass
• Seitenzahl: 792
• Erscheinungstermin: 9. Mai 2016
• Englisch
• ISBN-13: 9781118822357
• Artikelnr.: 45055724

Autorenporträt

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.

Inhaltsangabe

Preface xix About the Editor xxiii Contributors xxv Chapter 1 Biocatalysis and Green Chemistry 1 Roger A. Sheldon 1.1 Introduction to Sustainable Development and Green Chemistry 1 1.2 Green Chemistry Metrics 2 1.3 Environmental Impact and Sustainability Metrics 4 1.4 Solvents 5 1.5 The Role of Catalysis 6 1.6 Biocatalysis and Green Chemistry 6 1.7 Examples of Green Biocatalytic Processes 8 1.8 Conclusions and Future Prospects 13 Chapter 2 Enzymatic Synthesis of Chiral Amines using
-Transaminases, Amine Oxidases, and the Berberine Bridge Enzyme 17 Eduardo Busto, Robert C. Simon, Nina Richter, and Wolfgang Kroutil 2.1 Introduction 17 2.2 Synthesis of Chiral Amines using
?]Transaminases 18 2.3 Amine Oxidases 34 2.4 Berberine Bridge Enzymes 50 2.5 Conclusions 52 Chapter 3 Decarboxylation and Racemization of Unnatural Compounds using Artificial Enzymes Derived from Arylmalonate Decarboxylase 59 Kenji Miyamoto 3.1 Introduction 59 3.2 Discovery of a Bacterial
?]Aryl?]
?]Methylmalonate Decarboxylase 61 3.3 Purification and Characterization of the Decarboxylase (Amdase) 61 3.4 Cloning of the Amdase Gene 62 3.5 Stereochemical Course of Amdase?]Catalyzed Decarboxylation 62 3.6 Directed Evolution of Amdase to an Artificial Profen Racemase 63 3.7 Inversion of Enantioselectivity Dramatically Improves Catalytic Activity 65 3.8 Future Prospects 68 Chapter 4 Green Processes for the Synthesis of Chiral Intermediates for the Development of Drugs 71 Ramesh N. Patel 4.1 Introduction 71 4.2 Saxagliptin: Enzymatic Synthesis of (S)?]N?]Boc?]3?]Hydroxyadamantylglycine 71 4.3 Sitagliptin: Enzymatic Synthesis of Chiral Amine 72 4.4 Vanlev: Enzymatic Synthesis of (S)?]6?]Hydroxynorleucine 73 4.5 Vanlev: Enzymatic Synthesis of Allysine Ethylene Acetal 74 4.6 Vanlev: Enzymatic Synthesis of Thiazepine 74 4.7 Tigemonam: Enzymatic Synthesis of (S)?]ß?]Hydroxyvaline 76 4.8 Autoimmune Diseases: Enzymatic Synthesis of (S)?]Neopentylglycine 76 4.9 Atazanavir: Enzymatic Synthesis of (S)?]Tertiary Leucine 77 4.10 Thrombin Inhibitor (Inogatran): Synthesis of (R)?]Cyclohexylalanine 78 4.11 Gamma Secretase Inhibitor: Enzymatic Synthesis of (R)?]5,5,5?]Trifluoronorvaline 79 4.12 NK1/NK2 Dual Antagonists: Enzymatic Desymmetrization of Diethyl 3?][3
,4
?]Dichlorophenyl] Glutarate 80 4.13 Pregabalin: Enzymatic Synthesis of Ethyl (S)?]3?]Cyano?]5?]Methylhexanoate 81 4.14 Chemokine Receptor Modulator: Enzymatic Synthesis of (1S,2R)?]2?](Methoxycarbonyl)-Cyclohex?]4?]ene?]1?]Carboxylic Acid 82 4.15 Enzymatic Synthesis of (3S,5R)?]3?](Aminomethyl)?]5?]Methyloctanoic Acid 82 4.16 Atorvastatin (Lipitor): Enzymatic Desymmetrization of 3?]Hydroxyglutaronitrile 83 4.17 Anticancer Drugs: Enzymatic Synthesis of Taxane Side Chain 84 4.18 Antidiabetic and CNS Drugs: Enzymatic Hydrolysis of Dimethyl Bicyclo[2.2.1] Heptane?]1,4?]Dicarboxylate 85 4.19 Clopidogrel (Plavix): Enzymatic Preparation of 2?]Chloromandelic Acid Esters 85 4.20 Antiviral Drug: Regioselective Enzymatic Acylation of Ribavirin 86 4.21 Anticholesterol Drug: Enzymatic Acylation of Alcohol 87 4.22 Saxagliptin: Enzymatic Synthesis of (5S)?]4,5?]Dihydro?]1H?]Pyrrole?]1,5 Dicarboxylic Acid, 1?](1,1?]Dimethylethyl)?]5?]Ethyl Ester 88 4.23 Montelukast: Synthesis of Intermediate for LTD4 Antagonists 89 4.24 Atazanavir: Enzymatic Synthesis of (1S,2R)?][3?]Chloro?]2?]Hydroxy?]1 (Phenylmethyl) Propyl]?]Carbamic Acid,1,1?]Dimethyl?]Ethyl Ester 90 4.25 Atorvastatin: Enzymatic Synthesis of (R)?]4?]Cyano?]3?]Hydroxybutyrate 91 4.26 Antianxiety Drug: Enzymatic Synthesis of 6?]Hydroxybuspirone 92 4.27 Protease Inhibitor: Enzymatic Synthesis of (R)?]3?](4?]Fluorophenyl)?]2?]Hydroxy Propionic Acid 93 4.28 Dermatological and Anticancer Drugs: Enzymatic Synthesis of 2?](R)?]Hydroxy?]2?](1
,2
,3
, 4
?]Tetrahydro?]1
,1
,4
,4
?]Tetramethyl?]6
?]Naphthalenyl) Acetate 94 4.29 Antipsychotic Drug: Enzymatic Reduction of 1?](4?]Fluorophenyl)4?][4?](5?]Fluoro?]2?]Pyrimidinyl)1?]Piperazinyl]?]1?]Butanone 95 4.30 Cholesterol?]Lowering Agents: Enzymatic Synthesis of (3S,5R)?]Dihydroxy?]6?](Benzyloxy) Hexanoic Acid, Ethyl Ester 95 4.31 Antimigraine Drugs: Enzymatic Synthesis of (R)?]2?]Amino?]3?](7?]Methyl?]1H?]Indazol?]5?]yl) Propanoic Acid 96 4.32 Antidiabetic Drug (GLP?]1 Mimics): Enzymatic Synthesis of (S)?]Amino?]3?][3?]{6?](2?]Methylphenyl)} Pyridyl]?]Propionic Acid 97 4.33 Ephedrine: Synthesis of (R)?]Phenylacetylcarbinol 98 4.34 Zanamivir: Enzymatic Synthesis of N?]Acetylneuraminic Acid 99 4.35 Epivir: Enzymatic Deamination Process for the Synthesis of (2
R?]cis)?]2
?]Deoxy?]3?]Thiacytidine 100 4.36 HMG?]CoA Reductase Inhibitors: Aldolase?]Catalyzed Synthesis of Chiral Lactol 101 4.37 Boceprevir: Oxidation of 6,6?]Dimethyl?]3?]Azabicyclo[3.1.0]Hexane by Monoamine Oxidase 102 4.38 Crixivan: Enzymatic Synthesis of Indandiols 103 4.39 Potassium Channel Opener: Preparation of Chiral Epoxide and trans?]Diol 104 4.40 Epothilones (Anticancer Drugs): Epothilone B and Epothilone F 105 4.41 ß?]Adrenergic Blocking Agents: Synthesis of Intermediates for Propranolol and Denopamine 106 4.42 Conclusion 106 Chapter 5 Dynamic Kinetic Resolution of Alcohols, Amines, and Amino Acids 115 Jusuk Lee, Yoon Kyung Choi, Jaiwook Park, and Mahn?]Joo Kim 5.1 Introduction 115 5.2 Dynamic Kinetic Resolution of Secondary Alcohols 119 5.3 Dynamic Kinetic Resolution of Amines and Amino Acids 133 5.4 Applications of Dynamic Kinetic Resolution 139 5.5 Summary 145 Appendix: List of Abbreviations 145 Chapter 6 Recent Developments in Flavin-Based Catalysis: Enzymatic Sulfoxidation 149 Patricia B. Brondani, Marco W. Fraaije, and Gonzalo de Gonzalo 6.1 Introduction 149 6.2 Enzymatic Sulfoxidation Catalyzed by Flavoprotein Oxidases 150 6.3 Use of Flavoprotein Monooxygenases for the Synthesis of Chiral Sulfoxides 151 6.4 Asymmetric Sulfoxidation using Flavins as Catalysts 160 6.5 Summary and Outlook 162 Chapter 7 Development of Chemoenzymatic Processes: An Industrial Perspective 165 Rajesh Kumar, Carlos Martinez, Van Martin, and John Wong 7.1 Introduction 165 7.2 Synthetic Route Design and Integration of Biocatalysis 166 7.3 Screening and Biocatalyst Selection 169 7.4 Chemoenzymatic Process Development 169 7.5 Conclusions 176 Chapter 8 Epoxide Hydrolases and their Application in Organic Synthesis 179 Alain Archelas, Gilles Iacazio, and Michael Kotik 8.1 Introduction 179 8.2 Sources and Reaction Mechanism of EHs 181 8.3 Directed Evolution and Genetic Engineering of EHs 183 8.4 Immobilized EHs and Reactions in Nonaqueous Media 186 8.5 Monofunctional Epoxides as Chiral Building Blocks for the Synthesis of Biologically Active Compounds 188 8.6 Preparation of Valuable Chiral Building Blocks for the Synthesis of Biologically Active Compounds Starting from Bifunctional Epoxides 204 8.7 Application to Natural Product Synthesis 210 8.8 Bienzymatic Process Implying One Epoxide Hydrolase 216 8.9 Conclusions 219 Chapter 9 Enantioselective Acylation of Alcohol and Amine Reactions in Organic Synthesis 231 Vicente Gotor?]Fernández and Vicente Gotor 9.1 Introduction 231 9.2 Enantioselective Acylation of Alcohols 234 9.3 Acylation of Amines 248 9.4 Conclusions 260 Chapter 10 Recent Advances in Enzyme-Catalyzed Aldol Addition Reactions 267 Pere Clapés 10.1 Introduction 267 10.2 Pyruvate-Dependent Aldolases 269 10.3 Dihydroxyacetone Phosphate (DHAP)-Dependent Aldolases, d-Fructose-6-Phosphate Aldolase (FSA) and Transaldolases 276 10.4 Threonine Aldolases 287 10.5 Aldol Type Reactions Catalyzed by Non?]Aldolases 293 10.6 Computational De Novo Enzyme Design 294 10.7 Conclusions and Perspectives 295 Chapter 11 Enzymatic Asymmetric Reduction of Carbonyl Compounds 307 Tomoko Matsuda, Rio Yamanaka, and Kaoru Nakamura 11.1 Introduction 307 11.2 Mechanisms 307 11.3 Preparation of Biocatalysts 309 11.4 Solvent Engineering 316 11.5 Examples for Biocatalytic Asymmetric Reductions 317 11.6 Conclusions 325 Chapter 12 Nitrile?]Converting Enzymes and their Synthetic Applications 331 Ludmila Martínková 12.1 Introduction 331 12.2 Screening Methodology 332 12.3 Nitrilases 333 12.4 Nitrile Hydratases 340 12.5 Conclusions 343 Acknowledgements 343 Chapter 13 Biocatalytic Epoxidation for Green Synthesis 351 Hui Lin, Meng?]Yu Xu, Yan Liu, and Zhong?]Liu Wu 13.1 Introduction 351 13.2 Enzymes for Asymmetric Epoxidation 352 13.3 Application of Bioepoxidation in Organic Synthesis 354 13.4 Protein Engineering for Biocatalytic Epoxidation Reaction 362 13.5 Conclusions and Outlook 367 Acknowledgments 368 Chapter 14 Dynamic Kinetic Resolution via Hydrolase-Metal Combo Catalysis 373 Pilar Hoyos, Vittorio Pace, María J. Hernáiz, and Andrés R. Alcántara 14.1 Introduction 373 14.2 DKR of Secondary Alcohols 374 14.3 DKR of Amines 386 14.4 Conclusion 391 Chapter 15 Discovery and Engineering of Enzymes for Peptide Synthesis and Activation 397 Ana Toplak, Muhammad I. Arif, Bian Wu, and Dick B. Janssen 15.1 Introduction 397 15.2 Classification of Enzymes for Peptide Coupling 399 15.3 Serine and Cysteine Proteases for Peptide Synthesis 402 15.4 Protease Discovery 409 15.5 Proteases Engineered for Improved Synthesis 410 15.6 Enzymes for Peptide Terminal Modification 412 15.7 Conclusions 415 Chapter 16 Biocatalysis for Drug Discovery and Development 421 Youyun Liang, Mingzi M. Zhang, Ee Lui Ang, and Huimin Zhao 16.1 Introduction 421 16.2 Single Enzymatic Reactions 423 16.3 Multienzyme Biocatalytic Reactions 437 16.4 Future Perspective: Biocatalysts for the Pharmaceutical Industry 445 16.5 Conclusion 448 Chapter 17 Application of Aromatic Hydrocarbon Dioxygenases 457 Watumesa A. Tan and Rebecca E. Parales 17.1 Introduction 457 17.2 Challenges in Aromatic Hydrocarbon Dioxygenase Applications 457 17.3 Protein Engineering to Improve Enzymatic Activity and Alter Substrate Specificity 459 17.4 Protein Engineering for the Production of Specific Chemicals 464 17.5 Strain Modification for the Development of New Biodegradation Pathways 467 17.6 Phytoremediation: The Expression of Bacterial Dioxygenases in Plant Systems for Bioremediation Purposes 468 17.7 Concluding Remarks 469 Acknowledgments 469 Chapter 18 Ene?]reductases and their Applications 473 Tanja Knaus, Helen S. Toogood, and Nigel S. Scrutton 18.1 Introduction 473 18.2 Substrate Classes and Industrial Applications 474 18.3 Multienzyme Reactions 478 18.4 Alternative Hydride Sources 479 18.5 Improvements of Productivity, Stereoselectivity, and/or Conversion 482 Chapter 19 Recent Developments in Aminopeptidases, Racemases, and Oxidases 489 Yasuhisa Asano, Seiji Okazaki, and Kazuyuki Yasukawa 19.1 Aminopeptidase 489 19.2 Racemase 492 19.3 Amino Acid Oxidase 495 Chapter 20 Biocatalytic Cascades for API Synthesis 503 John M. Woodley 20.1 Introduction 503 20.2 Multienzymatic Biocatalysis 504 20.3 Process Aspects for Multistep Biocatalysis 506 20.4 Process Development 511 20.5 Biocatalytic Cascade Examples 512 20.6 Future Outlook 515 Chapter 21 Yeast-Mediated Stereoselective Synthesis 519 René Csuk 21.1 Introduction 519 21.2 Reductions of Aldehydes and Ketones 521 21.3 Reduction of Thiocarbonyls or Sulfur?]Containing Compounds 524 21.4 Reduction of Functionalized Carbonyl and Dicarbonyl Compounds 524 21.5 Reduction of Keto Esters 527 21.6 Hydrolysis of Esters 529 21.7 Immobilized Baker's Yeast 530 21.8 Whole?]Cell Biocatalysis in Ionic Liquids and Deep Eutectic Solvents 531 21.9 C"C Bond?]Forming and Breaking Reactions 532 21.10 Miscellaneous Reactions 533 21.11 Conclusions 534 Chapter 22 Biocatalytic Introduction of Chiral Hydroxy Groups using Oxygenases and Hydratases 545 Jun Ogawa, Makoto Hibi, and Shigenobu Kishino 22.1 Introduction 545 22.2 Regio?] and Stereoselective Hydroxylation of Propylbenzene and 3?]Chlorostyrene by Cytochrome P450 BM?]3 and its Mutant 546 22.3 Regio?] and Stereoselective Hydroxylation of Aliphatic Amino Acids by Fe(Ii)/
?]Ketoglutarate?]Dependent Dioxygenases 547 22.4 Regio?] and Stereoselective Hydration of Unsaturated Fatty Acids by a Novel Fatty Acid Hydratase 551 22.5 Conclusion 553 Acknowledgment 553 Chapter 23 Asymmetric Synthesis with Recombinant Whole?]Cell Catalyst 557 Harald Gröger, Werner Hummel, and Severin Wedde 23.1 Introduction 557 23.2 The Design/Construction of Whole?]Cell Catalysts 558 23.3 Biotransformations with Whole?]Cell Catalysts 561 23.4 Conclusion 581 Chapter 24 Lipases and Esterases as User-Friendly Biocatalysts in Natural Product Synthesis 587 Kenji Mori 24.1 Introduction 587 24.2 Desymmetrization of Prochiral or meso?]Diols and Diacetates 587 24.3 Kinetic Resolution of Racemic Alcohols 592 24.4 Preparation of Enantiopure Intermediate(s) from a Mixture of Stereoisomers 599 24.5 Conclusion 601 Acknowledgments 601 Chapter 25 Hydroxynitrile Lyases for Biocatalytic Synthesis of Chiral Cyanohydrins 603 Romana Wiedner, Helmut Schwab, and Kerstin Steiner 25.1 Introduction 603 25.2 Discovery of Hydroxynitrile Lyases: Bioprospecting 604 25.3 Applications of Hydroxynitrile Lyases 609 25.4 Structural and Mechanistic Aspects 611 25.5 Engineering of Hydroxynitrile Lyases 612 25.6 Reaction Engineering and Reaction Systems 620 25.7 Conclusion 623 Acknowledgment 623 Chapter 26 Biocatalysis: Nitrilases in Organic Synthesis 629 Jin?]Song Gong, Jin?]Song Shi, and Zheng?]Hong Xu 26.1 Introduction 629 26.2 Nitrilase Discovery 630 26.3 Nitrilase Improvement 631 26.4 Applications in Organic Synthesis 635 26.5 Conclusions and Future Prospects 638 Acknowledgments 639 Chapter 27 Biotechnology for the Production of Chemicals, Intermediates, and Pharmaceutical Ingredients 643 Hans?]Peter Meyer 27.1 Introduction 643 27.2 Value Chains and Markets 645 27.3 The Toolbox 661 27.4 Sustainability, Green Premium Pricing, and Subsidies 665 27.5 Regulatory Aspects and Public Perception 667 27.6 Innovation (Not Only in the Laboratory!) 669 27.7 Conclusions 670 Acknowledgments 671 Chapter 28 Microbial Transformations of Pentacyclic Triterpenes 675 Robert Azerad 28.1 Introduction 675 28.2 Typical Biotransformations in the Lupane Family 677 28.3 Typical Biotransformations in the Oleane Family 680 28.4 Typical Biotransformations in the Ursane Family 692 28.5 Microbial Transformations of Other Pts 704 28.6 Glycosylations and Deglycosylations 704 28.7 Conclusion and Perspectives 710 Chapter 29 Transaminases and their Applications 715 Sarah-Marie Dold, Christoph Syldatk, and Jens Rudat 29.1 Introduction 715 29.2 General Properties of Transaminases 715 29.3 Synthesis Strategies with Transaminases 719 29.4 Approaches to Optimize the Transaminase?]Catalyzed Reactions 735 29.5 Conclusion 743 Index 747