Future Directions in Biocatalysis 1st Edition by Tomoko Matsuda 9780444530592 0444530592

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ISBN 10: 0444530592

ISBN 13: 9780444530592

Author: Tomoko Matsuda

In Future Directions in Biocatalysis the important topics within biocatalysis and enzymatic catalysis for organic synthesis are described for both experts and non-experts. This books focuses particularly on reactions under development at present and on future advances in the field.

Consisting of four sections, this book examines enzymatic reactions under unusual conditions, unique biocatalytic reactions, synthesis of valuable compounds using biocatalysis and the latest molecular biology methods for biocatalysis. Each chapter deals with a specific theme and includes a summary of each area as well as the present state and future direction of research.

* Describes methods for solving environmental issues through biocatalysis
* Presents the integrated fields of biochemistry and organic chemistry
* Unique research topics with high originality

Table of contents:

CHAPTER 1 Biotransformation in ionic liquid

1. Introduction

2. Ionic Liquids as a Reaction Medium for Biotransformation

3. Lipase-Catalyzed Reaction in an Ionic Liquid Solvent System

4. Activation of Lipase by an Ionic Liquid

5. Various Biotransformations in an Ionic Liquid Solvent System

6. Concluding Remarks

References

CHAPTER 2 Temperature control of the enantioselectivity in the lipase-catalyzed resolutions

1. Introduction

2. Finding of the Low-Temperature MethodŽ in the Lipase-Catalyzed Kinetic Resolution

3. Theory of Temperature Effect on the Enantioselectivity

4. General Applicability of the Low-Temperature MethodŽ Examined

4.1. Application to solketal and other primary and secondary alcohols

4.2. Resolution of (±)-2-hydroxy-2-(pentafluorophenyl)acetonitrile

4.3. Immobilization of lipase on porous ceramic support (Toyonite) for acceleration

4.4. Structural optimization of organic bridges on Toyonite

4.5. Practical resolution of azirine 1 by the low-temperature methodŽ combined with Toyonite-immo

4.6. Resolution of (2R*, 3S*)- and (2R*, 3R*)-3-methyl-3-phenyl-2-aziridinemethanols

4.7. Resolution of 5-(hydroxymethyl)-3-phenyl-2-isoxazoline

4.8. Application of temperature control to asymmetric protonation

4.9. Lipase-catalyzed resolutions at high temperatures up to 120°C

5. Low-Temperature Reactions in Literatures

6. Lipase-Catalyzed Resolution of Primary Alcohols: Promising Candidates for the Low-Temperature M

7. Conclusion

References

CHAPTER 3 Future directions in photosynthetic organisms-catalyzed reactions

1. Introduction

2. Reduction Reaction

3. Oxidation and Hydroxylation

4. Removal of Organic and Inorganic Substances in Wastewater

5. Conclusion

References

CHAPTER 4 Catalysis by enzyme–metal combinations

1. Introduction

2. Dynamic Kinetic Resolutions by Enzyme–Metal Combinations

2.1. DKR of secondary alcohols

3. Asymmetric Transformations by Enzyme–Metal Combinations

3.1. Asymmetric transformation of ketone

3.2. Asymmetric transformation of enol ester

3.3. Asymmetric transformation of ketoxime

4. Conclusion

Acknowledgements

References

Part 2 Uncomon kind of biocatalytic reaction

CHAPTER 5 Biological Kolbe–Schmitt carboxylation

1. Introduction

2. Enzymes Catalyzing the Carboxylation of Phenolic Compounds

2.1. 4-Hydroxybenzoate decarboxylase (EC 4.1.1.61)

2.2. 3,4-Dihydroxybenzoate decarboxylase (EC 4.1.1.63)

2.3. Phenolphosphate carboxylase (EC 4.1.1.-) in Thauera aromatica

2.4. 2,6-Dihydroxybenzoate decarboxylase

2.5. 2,3-Dihydroxybenzoate decarboxylase

3. Enzymes Catalyzing the Direct Carboxylation of Heterocyclic Compounds

3.1. Pyrrole-2-carboxylate decarboxylase

3.2. Indole-3-carboxylate decarboxylase

4. Structure Analysis of Decarboxylases Catalyzing CO2 Fixation

4.1. Class I decarboxylases

4.2. Class II decarboxylases

4.3. Phenylphosphate carboxylase

5. Conclusion

References

CHAPTER 6 Discovery, redesign and applications of Baeyer–Villiger monooxygenases

1. Introduction

2. Biocatalytic Properties of Recombinant Available BVMOs

2.1. Discovery of novel BVMOs

2.2. Exploring sequenced (meta)genomes for novel BVMOs

2.3. Screening the metagenome for novel BVMOs

2.4. Redesign of BVMOs

3. Conclusions: Future Directions

References

CHAPTER 7 Enzymes in aldoxime–nitrile pathway: versatile tools in biocatalysis

1. Introduction

2. Screening for New Microbial Enzymes by Enrichment and Acclimation Culture Techniques

3. Development of Nitrile-Degrading Enzymes

4. Screening for Heat-Stable NHase

5. Screening for NHase with PCR

6. Nitrile Synthesis Using a New Enzyme, Aldoxime Dehydratase

6.1. Aldoxime-converting enzymes

6.2. Isolation of microorganisms having aldoxime dehydratase activity

6.3. Purification, characterization and primary structure determination of aldoxime dehydratase

6.4. Synthesis of nitriles from aldoxime with aldoxime dehydratase

6.5. Distribution of aldoxime dehydratase

6.6. Molecular screening for aldoxime…nitrile pathwayŽ

7. Conclusions

Acknowledgements

References

CHAPTER 8 Addition of hydrocyanic acid to carbonyl compounds

1. Introduction

2. Optimized Reaction Conditions for the HNL-Catalyzed Formation of Chiral Cyanohydrins

3. Synthetic Potential of Chiral Cyanohydrins in Stereoselective Synthesis

3.1. Chiral 2-hydroxy carboxylic acids

3.2. Optically active 1,2-amino alcohols

3.3. Stereoselective substitution of the hydroxyl group in chiral cyanohydrins

3.4. Stereoselective synthesis of substituted cyclohexanone cyanohydrins

4. Crystal Structures of Hydroxynitrile Lyases and Mechanism of Cyanogenesis

4.1. Crystal structures of HNLs

4.2. Reaction mechanism of cyanogenesis

4.3. Changing substrate specificity and stereoselectivity applying Trp128 mutants of wt-MeHNL

5. Conclusions

References

Part 3 Novel compounds synthesized by biotransformations

CHAPTER 9 Chiral heteroatom-containing compounds

1. Introduction

2. Organosulfur Compounds

2.1. C-chiral hydroxy sulfides and derivatives

2.2. C-chiral hydroxyalkyl sulfones

2.3. C-chiral alkyl sulfates

2.4. Other C-chiral organosulfur compounds

2.5. S-chiral sulfinylcarboxylates

2.6. S-chiral hydroxy sulfoxides

2.7. S-chiral sulfinamides

2.8. S-chiral sulfoximines

3. Organophosphorus Compounds

3.1. C-chiral hydroxy phosphorus derivatives

3.2. C-chiral amino phosphorus compounds

3.3. P-chiral phosphoro-acetates

3.4. P-chiral hydroxy phosphoryl compounds

3.5. P-chiral hydroxy phosphorus P-boranes

3.6. Stereocontrolled transformations of organophosphorus acid esters

4. Organosilanes

5. Organogermanes

6. Future Perspectives

References

CHAPTER 10 Enzymatic polymerization

1. Introduction

2. Enzymatic Synthesis of Polyesters

2.1. Ring-opening polymerization to polyesters

2.2. Polycondensation of dicarboxylic acid derivatives and glycols to polyesters

2.3. Enzymatic synthesis of functional polyesters

3. Enzymatic Synthesis of Phenolic Polymers

3.1. Enzymatic oxidative polymerization of phenols

3.2. Enzymatic synthesis of functional phenolic polymers

3.3. Artificial urushi

3.4. Enzymatic synthesis and biological properties of flavonoid polymers

4. Concluding Remarks

References

CHAPTER 11 Synthesis of naturally occurring β-D-glucopyranosides based on enzymatic β-glucosidatio

1. Introduction

2. Synthesis of β-D-Glucopyranoside Under Kinetically Controlled Condition

2.1. Synthesis of naturally occurring β-D-glucopyranoside

3. Synthesis of β-D-Glucopyranoside Under Equilibrium-Controlled Condition

3.1. Immobilization of β-D-glucosidase using prepolymer

3.2. Enzymatic transglucosidation

3.3. Synthesis of naturally occurring benzyl β-D-glucopyranoside

3.4. Synthesis of phenethyl β-D-glucopyranoside

3.5. Synthesis of (3Z)-hexenyl β-D-glucopyranoside

3.6. Synthesis of geranyl β-D-glucopyranoside

3.7. Synthesis of Sacranosides A (89) and B (90)

3.8. Synthesis of naturally occurring n-octyl β-D-glucopyranosides

3.9. Synthesis of naturally occurring hexyl β-D-glucopyranosides

3.10. Synthesis of naturally occurring phenylpropenoid β-D-glucopyranoside

4. Future Aspect

5. Conclusion

References

Part 4 Use of molecular biology technique to find novel biocatalyst

CHAPTER 12 Future directions in alcohol dehydrogenase-catalyzed reactions

1. Introduction

2. Future Progress in the Discovery Phase of Dehydrogenases

2.1. Accurately predicting dehydrogenase structures

2.2. Predicting dehydrogenase substrate acceptance and stereoselectivities

2.3. Rapid screening of novel dehydrogenases

2.4. Dehydrogenases for large substrates

2.5. Dehydrogenase modules within larger assemblies as monofunctional catalysts

2.6. Dehydrogenase catalysis of other 1,2-carbonyl additions

3. Future Progress in Dehydrogenase Process Development

3.1. Improving the kinetic properties of dehydrogenases

3.2. Reductions of highly hydrophobic substrates

3.3. Cofactorless dehydrogenases?

4. Conclusions

Acknowledgements

References

CHAPTER 13 Enzymatic decarboxylation of synthetic compounds

1. Introduction

2. Arylmalonate Decarboxylase

2.1. Discovery of arylmalonate decarboxylase and its substrate specificity

2.2. Purification of the enzyme and cloning of the gene

2.3. Reaction mechanism

2.4. Inversion of enantioselectivity based on the reaction mechanism and homology

2.5. Addition of racemase activity

3. Transketolase-Catalyzed Reaction

3.1. Substrate specificity and stereochemical source of TKase-catalyzed reaction

3.2. Application of TKase-catalyzed reaction in organic syntheses

3.3. Tertiary structure and mutagenesis studies

4. Future Trends of this Area

4.1. Application of decarboxylation reaction to dialkylmalonates

4.2. Decarboxylation of various carboxylic acids

4.3. Oxidative decarboxylation of β-hydroxycarboxylic acids

4.4. Carboxylation

4.5. Development of biotransformation via enolate

4.6. Utilization of database and informatics

5. Conclusion

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