Green Biocatalysis -  - ebook

Green Biocatalysis ebook

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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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Table of Contents

Cover

Title Page

Preface

About the Editor

Contributors

CHAPTER 1: Biocatalysis and Green Chemistry

1.1 INTRODUCTION TO SUSTAINABLE DEVELOPMENT AND GREEN CHEMISTRY

1.2 GREEN CHEMISTRY METRICS

1.3 ENVIRONMENTAL IMPACT AND SUSTAINABILITY METRICS

1.4 SOLVENTS

1.5 THE ROLE OF CATALYSIS

1.6 BIOCATALYSIS AND GREEN CHEMISTRY

1.7 EXAMPLES OF GREEN BIOCATALYTIC PROCESSES

1.8 CONCLUSIONS AND FUTURE PROSPECTS

REFERENCES

CHAPTER 2: Enzymatic Synthesis of Chiral Amines using ω-Transaminases, Amine Oxidases, and the Berberine Bridge Enzyme

2.1 INTRODUCTION

2.2 SYNTHESIS OF CHIRAL AMINES USING ω-TRANSAMINASES

2.3 AMINE OXIDASES

2.4 BERBERINE BRIDGE ENZYMES

2.5 CONCLUSIONS

REFERENCES

CHAPTER 3: Decarboxylation and Racemization of Unnatural Compounds using Artificial Enzymes Derived from Arylmalonate Decarboxylase

3.1 INTRODUCTION

3.2 DISCOVERY OF A BACTERIAL α-ARYL-α-METHYLMALONATE DECARBOXYLASE

3.3 PURIFICATION AND CHARACTERIZATION OF THE DECARBOXYLASE (AMD

ASE

)

3.4 CLONING OF THE AMD

ASE

GENE

3.5 STEREOCHEMICAL COURSE OF AMD

ASE

-CATALYZED DECARBOXYLATION

3.6 DIRECTED EVOLUTION OF AMD

ASE

TO AN ARTIFICIAL PROFEN RACEMASE

3.7 INVERSION OF ENANTIOSELECTIVITY DRAMATICALLY IMPROVES CATALYTIC ACTIVITY

3.8 FUTURE PROSPECTS

REFERENCES

CHAPTER 4: Green Processes for the Synthesis of Chiral Intermediates for the Development of Drugs

4.1 INTRODUCTION

4.2 SAXAGLIPTIN: ENZYMATIC SYNTHESIS OF (

S

)-

N

-BOC-3-HYDROXYADAMANTYLGLYCINE

4.3 SITAGLIPTIN: ENZYMATIC SYNTHESIS OF CHIRAL AMINE

4.4 VANLEV: ENZYMATIC SYNTHESIS OF(

S

)-6-HYDROXYNORLEUCINE

4.5 VANLEV: ENZYMATIC SYNTHESIS OF ALLYSINE ETHYLENE ACETAL

4.6 VANLEV: ENZYMATIC SYNTHESIS OF THIAZEPINE

4.7 TIGEMONAM: ENZYMATIC SYNTHESIS OF (

S

)-β-HYDROXYVALINE

4.8 AUTOIMMUNE DISEASES: ENZYMATIC SYNTHESIS OF (

S

)-NEOPENTYLGLYCINE

4.9 ATAZANAVIR: ENZYMATIC SYNTHESIS OF (

S

)-TERTIARY LEUCINE

4.10 THROMBIN INHIBITOR (INOGATRAN): SYNTHESIS OF (

R

)-CYCLOHEXYLALANINE

4.11 GAMMA SECRETASE INHIBITOR: ENZYMATIC SYNTHESIS OF (

R

)-5,5,5-TRIFLUORONORVALINE

4.12 NK1/NK2 DUAL ANTAGONISTS: ENZYMATIC DESYMMETRIZATION OF DIETHYL 3-[3′,4′-DICHLOROPHENYL] GLUTARATE

4.13 PREGABALIN: ENZYMATIC SYNTHESIS OF ETHYL (

S

)-3-CYANO-5-METHYLHEXANOATE

4.14 CHEMOKINE RECEPTOR MODULATOR: ENZYMATIC SYNTHESIS OF (1

S

,2

R

)-2-(METHOXYCARBONYL)CYCLOHEX-4-ENE-1-CARBOXYLIC ACID

4.15 ENZYMATIC SYNTHESIS OF (3

S

,5

R

)-3-(AMINOMETHYL)-5-METHYLOCTANOIC ACID

4.16 ATORVASTATIN (LIPITOR): ENZYMATIC DESYMMETRIZATION OF 3-HYDROXYGLUTARONITRILE

4.17 ANTICANCER DRUGS: ENZYMATIC SYNTHESIS OF TAXANE SIDE CHAIN

4.18 ANTIDIABETIC AND CNS DRUGS: ENZYMATIC HYDROLYSIS OF DIMETHYL BICYCLO[2.2.1]HEPTANE-1,4-DICARBOXYLATE

4.19 CLOPIDOGREL (PLAVIX): ENZYMATIC PREPARATION OF 2-CHLOROMANDELIC ACID ESTERS

4.20 ANTIVIRAL DRUG: REGIOSELECTIVE ENZYMATIC ACYLATION OF RIBAVIRIN

4.21 ANTICHOLESTEROL DRUG: ENZYMATIC ACYLATION OF ALCOHOL

4.22 SAXAGLIPTIN: ENZYMATIC SYNTHESIS OF (5

S

)-4,5-DIHYDRO-1

H

-PYRROLE-1,5 DICARBOXYLIC ACID, 1-(1,1-DIMETHYLETHYL)-5-ETHYL ESTER

4.23 MONTELUKAST: SYNTHESIS OF INTERMEDIATE FOR LTD4 ANTAGONISTS

4.24 ATAZANAVIR: ENZYMATIC SYNTHESIS OF (1

S

,2

R

)-[3-CHLORO-2-HYDROXY-1 (PHENYLMETHYL) PROPYL]-CARBAMIC ACID,1,1-DIMETHYL-ETHYL ESTER

4.25 ATORVASTATIN: ENZYMATIC SYNTHESIS OF (

R

)-4-CYANO-3-HYDROXYBUTYRATE

4.26 ANTIANXIETY DRUG: ENZYMATIC SYNTHESIS OF 6-HYDROXYBUSPIRONE

4.27 PROTEASE INHIBITOR: ENZYMATIC SYNTHESIS OF (

R

)-3-(4-FLUOROPHENYL)-2-HYDROXY PROPIONIC ACID

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

4.29 ANTIPSYCHOTIC DRUG: ENZYMATIC REDUCTION OF 1-(4-FLUOROPHENYL)4-[4-(5-FLUORO-2-PYRIMIDINYL)1-PIPERAZINYL]-1-BUTANONE

4.30 CHOLESTEROL-LOWERING AGENTS: ENZYMATIC SYNTHESIS OF (3

S

,5

R

)-DIHYDROXY-6-(BENZYLOXY) HEXANOIC ACID, ETHYL ESTER

4.31 ANTIMIGRAINE DRUGS: ENZYMATIC SYNTHESIS OF (

R

)-2-AMINO-3-(7-METHYL-1

H

-INDAZOL-5-YL) PROPANOIC ACID

4.32 ANTIDIABETIC DRUG (GLP-1 MIMICS): ENZYMATIC SYNTHESIS OF (

S

)-AMINO-3-[3-{6-(2-METHYLPHENYL)} PYRIDYL]-PROPIONIC ACID

4.33 EPHEDRINE: SYNTHESIS OF (

R

)-PHENYLACETYLCARBINOL

4.34 ZANAMIVIR: ENZYMATIC SYNTHESIS OF

N

-ACETYLNEURAMINIC ACID

4.35 EPIVIR: ENZYMATIC DEAMINATION PROCESS FOR THE SYNTHESIS OF (2′

R-CIS

)-2′-DEOXY-3-THIACYTIDINE

4.36 HMG-CoA REDUCTASE INHIBITORS: ALDOLASE-CATALYZED SYNTHESIS OF CHIRAL LACTOL

4.37 BOCEPREVIR: OXIDATION OF 6,6-DIMETHYL-3-AZABICYCLO[3.1.0]HEXANE BY MONOAMINE OXIDASE

4.38 CRIXIVAN: ENZYMATIC SYNTHESIS OF INDANDIOLS

4.39 POTASSIUM CHANNEL OPENER: PREPARATION OF CHIRAL EPOXIDE AND

TRANS

-DIOL

4.40 EPOTHILONES (ANTICANCER DRUGS): EPOTHILONE B AND EPOTHILONE F

4.41 β-ADRENERGIC BLOCKING AGENTS: SYNTHESIS OF INTERMEDIATES FOR PROPRANOLOL AND DENOPAMINE

4.42 CONCLUSION

REFERENCES

CHAPTER 5: Dynamic Kinetic Resolution of Alcohols, Amines, and Amino Acids

5.1 INTRODUCTION

5.2 DYNAMIC KINETIC RESOLUTION OF SECONDARY ALCOHOLS

5.3 DYNAMIC KINETIC RESOLUTION OF AMINES AND AMINO ACIDS

5.4 APPLICATIONS OF DYNAMIC KINETIC RESOLUTION

5.5 SUMMARY

APPENDIX: LIST OF ABBREVIATIONS

REFERENCES

CHAPTER 6: Recent Developments in Flavin-Based Catalysis

6.1 INTRODUCTION

6.2 ENZYMATIC SULFOXIDATION CATALYZED BY FLAVOPROTEIN OXIDASES

6.3 USE OF FLAVOPROTEIN MONOOXYGENASES FOR THE SYNTHESIS OF CHIRAL SULFOXIDES

6.4 ASYMMETRIC SULFOXIDATION USING FLAVINS AS CATALYSTS

6.5 SUMMARY AND OUTLOOK

REFERENCES

CHAPTER 7: Development of Chemoenzymatic Processes

7.1 INTRODUCTION

7.2 SYNTHETIC ROUTE DESIGN AND INTEGRATION OF BIOCATALYSIS

7.3 SCREENING AND BIOCATALYST SELECTION

7.4 CHEMOENZYMATIC PROCESS DEVELOPMENT

7.5 CONCLUSIONS

REFERENCES

CHAPTER 8: Epoxide Hydrolases and their Application in Organic Synthesis

8.1 INTRODUCTION

8.2 SOURCES AND REACTION MECHANISM OF EHs

8.3 DIRECTED EVOLUTION AND GENETIC ENGINEERING OF EHs

8.4 IMMOBILIZED EHs AND REACTIONS IN NONAQUEOUS MEDIA

8.5 MONOFUNCTIONAL EPOXIDES AS CHIRAL BUILDING BLOCKS FOR THE SYNTHESIS OF BIOLOGICALLY ACTIVE COMPOUNDS

8.6 PREPARATION OF VALUABLE CHIRAL BUILDING BLOCKS FOR THE SYNTHESIS OF BIOLOGICALLY ACTIVE COMPOUNDS STARTING FROM BIFUNCTIONAL EPOXIDES

8.7 APPLICATION TO NATURAL PRODUCT SYNTHESIS

8.8 BIENZYMATIC PROCESS IMPLYING ONE EPOXIDE HYDROLASE

8.9 CONCLUSIONS

REFERENCES

CHAPTER 9: Enantioselective Acylation of Alcohol and Amine Reactions in Organic Synthesis

9.1 INTRODUCTION

9.2 ENANTIOSELECTIVE ACYLATION OF ALCOHOLS

9.3 ACYLATION OF AMINES

9.4 CONCLUSIONS

REFERENCES

CHAPTER 10: Recent Advances in Enzyme-Catalyzed Aldol Addition Reactions

10.1 INTRODUCTION

10.2 PYRUVATE-DEPENDENT ALDOLASES

10.3 DIHYDROXYACETONE PHOSPHATE (DHAP)-DEPENDENT ALDOLASES,

D

-FRUCTOSE-6-PHOSPHATE ALDOLASE (FSA) AND TRANSALDOLASES

10.4 THREONINE ALDOLASES

10.5 ALDOL TYPE REACTIONS CATALYZED BY NON-ALDOLASES

10.6 COMPUTATIONAL

de novo

ENZYME DESIGN

10.7 CONCLUSIONS AND PERSPECTIVES

REFERENCES

CHAPTER 11: Enzymatic Asymmetric Reduction of Carbonyl Compounds

11.1 INTRODUCTION

11.2 MECHANISMS

11.3 PREPARATION OF BIOCATALYSTS

11.4 SOLVENT ENGINEERING

11.5 EXAMPLES FOR BIOCATALYTIC ASYMMETRIC REDUCTIONS

11.6 CONCLUSIONS

REFERENCES

CHAPTER 12: Nitrile-Converting Enzymes and their Synthetic Applications

12.1 INTRODUCTION

12.2 SCREENING METHODOLOGY

12.3 NITRILASES

12.4 NITRILE HYDRATASES

12.5 CONCLUSIONS

ACKNOWLEDGEMENTS

REFERENCES

CHAPTER 13: Biocatalytic Epoxidation for Green Synthesis

13.1 INTRODUCTION

13.2 ENZYMES FOR ASYMMETRIC EPOXIDATION

13.3 APPLICATION OF BIOEPOXIDATION IN ORGANIC SYNTHESIS

13.4 PROTEIN ENGINEERING FOR BIOCATALYTIC EPOXIDATION REACTION

13.5 CONCLUSIONS AND OUTLOOK

ACKNOWLEDGMENTS

REFERENCES

CHAPTER 14: Dynamic Kinetic Resolution via Hydrolase–Metal Combo Catalysis

14.1 INTRODUCTION

14.2 DKR OF SECONDARY ALCOHOLS

14.3 DKR OF AMINES

14.4 CONCLUSION

REFERENCES

CHAPTER 15: Discovery and Engineering of Enzymes for Peptide Synthesis and Activation

15.1 INTRODUCTION

15.2 CLASSIFICATION OF ENZYMES FOR PEPTIDE COUPLING

15.3 SERINE AND CYSTEINE PROTEASES FOR PEPTIDE SYNTHESIS

15.4 PROTEASE DISCOVERY

15.5 PROTEASES ENGINEERED FOR IMPROVED SYNTHESIS

15.6 ENZYMES FOR PEPTIDE TERMINAL MODIFICATION

15.7 CONCLUSIONS

REFERENCES

CHAPTER 16: Biocatalysis for Drug Discovery and Development

16.1 INTRODUCTION

16.2 SINGLE ENZYMATIC REACTIONS

16.3 MULTIENZYME BIOCATALYTIC REACTIONS

16.4 FUTURE PERSPECTIVE: BIOCATALYSTS FOR THE PHARMACEUTICAL INDUSTRY

16.5 CONCLUSION

REFERENCES

CHAPTER 17: Application of Aromatic Hydrocarbon Dioxygenases

17.1 INTRODUCTION

17.2 CHALLENGES IN AROMATIC HYDROCARBON DIOXYGENASE APPLICATIONS

17.3 PROTEIN ENGINEERING TO IMPROVE ENZYMATIC ACTIVITY AND ALTER SUBSTRATE SPECIFICITY

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