Elsevier S & T

Future Directions in Biocatalysis

Matsuda, Tomoko

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Table of contents
  • Cover
  • Table of Contentsv
  • Prefacexi
  • Part 1 Novel reaction conditions for biotransformation1
  • CHAPTER 1 Biotransformation in ionic liquid3
  • 1. Introduction3
  • 2. Ionic Liquids as a Reaction Medium for Biotransformation3
  • 3. Lipase-Catalyzed Reaction in an Ionic Liquid Solvent System7
  • 4. Activation of Lipase by an Ionic Liquid10
  • 5. Various Biotransformations in an Ionic Liquid Solvent System15
  • 6. Concluding Remarks18
  • References18
  • CHAPTER 2 Temperature control of the enantioselectivity in the lipase-catalyzed resolutions21
  • 1. Introduction21
  • 2. Finding of the Low-Temperature MethodŽ in the Lipase-Catalyzed Kinetic Resolution22
  • 3. Theory of Temperature Effect on the Enantioselectivity23
  • 4. General Applicability of the Low-Temperature MethodŽ Examined28
  • 4.1. Application to solketal and other primary and secondary alcohols28
  • 4.2. Resolution of (±)-2-hydroxy-2-(pentafluorophenyl)acetonitrile30
  • 4.3. Immobilization of lipase on porous ceramic support (Toyonite) for acceleration31
  • 4.4. Structural optimization of organic bridges on Toyonite32
  • 4.5. Practical resolution of azirine 1 by the low-temperature methodŽ combined with Toyonite-immo33
  • 4.6. Resolution of (2R*, 3S*)- and (2R*, 3R*)-3-methyl-3-phenyl-2-aziridinemethanols34
  • 4.7. Resolution of 5-(hydroxymethyl)-3-phenyl-2-isoxazoline36
  • 4.8. Application of temperature control to asymmetric protonation37
  • 4.9. Lipase-catalyzed resolutions at high temperatures up to 120°C37
  • 5. Low-Temperature Reactions in Literatures37
  • 6. Lipase-Catalyzed Resolution of Primary Alcohols: Promising Candidates for the Low-Temperature M40
  • 7. Conclusion45
  • References45
  • CHAPTER 3 Future directions in photosynthetic organisms-catalyzed reactions51
  • 1. Introduction51
  • 2. Reduction Reaction51
  • 3. Oxidation and Hydroxylation55
  • 4. Removal of Organic and Inorganic Substances in Wastewater56
  • 5. Conclusion57
  • References57
  • CHAPTER 4 Catalysis by enzyme–metal combinations59
  • 1. Introduction59
  • 2. Dynamic Kinetic Resolutions by Enzyme–Metal Combinations60
  • 2.1. DKR of secondary alcohols60
  • 3. Asymmetric Transformations by Enzyme–Metal Combinations73
  • 3.1. Asymmetric transformation of ketone73
  • 3.2. Asymmetric transformation of enol ester75
  • 3.3. Asymmetric transformation of ketoxime76
  • 4. Conclusion78
  • Acknowledgements78
  • References79
  • Part 2 Uncomon kind of biocatalytic reaction81
  • CHAPTER 5 Biological Kolbe–Schmitt carboxylation83
  • 1. Introduction83
  • 2. Enzymes Catalyzing the Carboxylation of Phenolic Compounds84
  • 2.1. 4-Hydroxybenzoate decarboxylase (EC 4.1.1.61)85
  • 2.2. 3,4-Dihydroxybenzoate decarboxylase (EC 4.1.1.63)87
  • 2.3. Phenolphosphate carboxylase (EC 4.1.1.-) in Thauera aromatica88
  • 2.4. 2,6-Dihydroxybenzoate decarboxylase91
  • 2.5. 2,3-Dihydroxybenzoate decarboxylase95
  • 3. Enzymes Catalyzing the Direct Carboxylation of Heterocyclic Compounds95
  • 3.1. Pyrrole-2-carboxylate decarboxylase96
  • 3.2. Indole-3-carboxylate decarboxylase99
  • 4. Structure Analysis of Decarboxylases Catalyzing CO2 Fixation101
  • 4.1. Class I decarboxylases102
  • 4.2. Class II decarboxylases103
  • 4.3. Phenylphosphate carboxylase103
  • 5. Conclusion103
  • References104
  • CHAPTER 6 Discovery, redesign and applications of Baeyer–Villiger monooxygenases107
  • 1. Introduction107
  • 2. Biocatalytic Properties of Recombinant Available BVMOs110
  • 2.1. Discovery of novel BVMOs112
  • 2.2. Exploring sequenced (meta)genomes for novel BVMOs114
  • 2.3. Screening the metagenome for novel BVMOs118
  • 2.4. Redesign of BVMOs119
  • 3. Conclusions: Future Directions122
  • References125
  • CHAPTER 7 Enzymes in aldoxime–nitrile pathway: versatile tools in biocatalysis129
  • 1. Introduction129
  • 2. Screening for New Microbial Enzymes by Enrichment and Acclimation Culture Techniques129
  • 3. Development of Nitrile-Degrading Enzymes131
  • 4. Screening for Heat-Stable NHase131
  • 5. Screening for NHase with PCR132
  • 6. Nitrile Synthesis Using a New Enzyme, Aldoxime Dehydratase133
  • 6.1. Aldoxime-converting enzymes133
  • 6.2. Isolation of microorganisms having aldoxime dehydratase activity134
  • 6.3. Purification, characterization and primary structure determination of aldoxime dehydratase134
  • 6.4. Synthesis of nitriles from aldoxime with aldoxime dehydratase135
  • 6.5. Distribution of aldoxime dehydratase136
  • 6.6. Molecular screening for aldoxime…nitrile pathwayŽ136
  • 7. Conclusions137
  • Acknowledgements137
  • References137
  • CHAPTER 8 Addition of hydrocyanic acid to carbonyl compounds141
  • 1. Introduction141
  • 2. Optimized Reaction Conditions for the HNL-Catalyzed Formation of Chiral Cyanohydrins143
  • 3. Synthetic Potential of Chiral Cyanohydrins in Stereoselective Synthesis145
  • 3.1. Chiral 2-hydroxy carboxylic acids145
  • 3.2. Optically active 1,2-amino alcohols147
  • 3.3. Stereoselective substitution of the hydroxyl group in chiral cyanohydrins148
  • 3.4. Stereoselective synthesis of substituted cyclohexanone cyanohydrins149
  • 4. Crystal Structures of Hydroxynitrile Lyases and Mechanism of Cyanogenesis149
  • 4.1. Crystal structures of HNLs151
  • 4.2. Reaction mechanism of cyanogenesis151
  • 4.3. Changing substrate specificity and stereoselectivity applying Trp128 mutants of wt-MeHNL152
  • 5. Conclusions153
  • References154
  • Part 3 Novel compounds synthesized by biotransformations157
  • CHAPTER 9 Chiral heteroatom-containing compounds159
  • 1. Introduction159
  • 2. Organosulfur Compounds160
  • 2.1. C-chiral hydroxy sulfides and derivatives160
  • 2.2. C-chiral hydroxyalkyl sulfones163
  • 2.3. C-chiral alkyl sulfates165
  • 2.4. Other C-chiral organosulfur compounds166
  • 2.5. S-chiral sulfinylcarboxylates166
  • 2.6. S-chiral hydroxy sulfoxides168
  • 2.7. S-chiral sulfinamides169
  • 2.8. S-chiral sulfoximines171
  • 3. Organophosphorus Compounds172
  • 3.1. C-chiral hydroxy phosphorus derivatives172
  • 3.2. C-chiral amino phosphorus compounds180
  • 3.3. P-chiral phosphoro-acetates183
  • 3.4. P-chiral hydroxy phosphoryl compounds186
  • 3.5. P-chiral hydroxy phosphorus P-boranes191
  • 3.6. Stereocontrolled transformations of organophosphorus acid esters192
  • 4. Organosilanes196
  • 5. Organogermanes197
  • 6. Future Perspectives197
  • References199
  • CHAPTER 10 Enzymatic polymerization205
  • 1. Introduction205
  • 2. Enzymatic Synthesis of Polyesters206
  • 2.1. Ring-opening polymerization to polyesters207
  • 2.2. Polycondensation of dicarboxylic acid derivatives and glycols to polyesters212
  • 2.3. Enzymatic synthesis of functional polyesters219
  • 3. Enzymatic Synthesis of Phenolic Polymers228
  • 3.1. Enzymatic oxidative polymerization of phenols228
  • 3.2. Enzymatic synthesis of functional phenolic polymers233
  • 3.3. Artificial urushi238
  • 3.4. Enzymatic synthesis and biological properties of flavonoid polymers240
  • 4. Concluding Remarks244
  • References245
  • CHAPTER 11 Synthesis of naturally occurring β-D-glucopyranosides based on enzymatic β-glucosidatio253
  • 1. Introduction253
  • 2. Synthesis of β-D-Glucopyranoside Under Kinetically Controlled Condition255
  • 2.1. Synthesis of naturally occurring β-D-glucopyranoside259
  • 3. Synthesis of β-D-Glucopyranoside Under Equilibrium-Controlled Condition262
  • 3.1. Immobilization of β-D-glucosidase using prepolymer263
  • 3.2. Enzymatic transglucosidation263
  • 3.3. Synthesis of naturally occurring benzyl β-D-glucopyranoside267
  • 3.4. Synthesis of phenethyl β-D-glucopyranoside270
  • 3.5. Synthesis of (3Z)-hexenyl β-D-glucopyranoside272
  • 3.6. Synthesis of geranyl β-D-glucopyranoside275
  • 3.7. Synthesis of Sacranosides A (89) and B (90)277
  • 3.8. Synthesis of naturally occurring n-octyl β-D-glucopyranosides278
  • 3.9. Synthesis of naturally occurring hexyl β-D-glucopyranosides280
  • 3.10. Synthesis of naturally occurring phenylpropenoid β-D-glucopyranoside282
  • 4. Future Aspect287
  • 5. Conclusion289
  • References289
  • Part 4 Use of molecular biology technique to find novel biocatalyst291
  • CHAPTER 12 Future directions in alcohol dehydrogenase-catalyzed reactions293
  • 1. Introduction293
  • 2. Future Progress in the Discovery Phase of Dehydrogenases295
  • 2.1. Accurately predicting dehydrogenase structures295
  • 2.2. Predicting dehydrogenase substrate acceptance and stereoselectivities296
  • 2.3. Rapid screening of novel dehydrogenases296
  • 2.4. Dehydrogenases for large substrates299
  • 2.5. Dehydrogenase modules within larger assemblies as monofunctional catalysts299
  • 2.6. Dehydrogenase catalysis of other 1,2-carbonyl additions300
  • 3. Future Progress in Dehydrogenase Process Development300
  • 3.1. Improving the kinetic properties of dehydrogenases301
  • 3.2. Reductions of highly hydrophobic substrates301
  • 3.3. Cofactorless dehydrogenases?302
  • 4. Conclusions302
  • Acknowledgements303
  • References303
  • CHAPTER 13 Enzymatic decarboxylation of synthetic compounds305
  • 1. Introduction305
  • 2. Arylmalonate Decarboxylase309
  • 2.1. Discovery of arylmalonate decarboxylase and its substrate specificity310
  • 2.2. Purification of the enzyme and cloning of the gene311
  • 2.3. Reaction mechanism312
  • 2.4. Inversion of enantioselectivity based on the reaction mechanism and homology317
  • 2.5. Addition of racemase activity319
  • 3. Transketolase-Catalyzed Reaction321
  • 3.1. Substrate specificity and stereochemical source of TKase-catalyzed reaction322
  • 3.2. Application of TKase-catalyzed reaction in organic syntheses322
  • 3.3. Tertiary structure and mutagenesis studies329
  • 4. Future Trends of this Area331
  • 4.1. Application of decarboxylation reaction to dialkylmalonates331
  • 4.2. Decarboxylation of various carboxylic acids332
  • 4.3. Oxidative decarboxylation of β-hydroxycarboxylic acids333
  • 4.4. Carboxylation336
  • 4.5. Development of biotransformation via enolate337
  • 4.6. Utilization of database and informatics339
  • 5. Conclusion339
  • References340
  • Index345
Book details
  • Vendor Elsevier S & T
  • SKU 9780444530592
  • ISBN-13 9780080545264
  • Author Matsuda, Tomoko
  • Category Science
  • Subject Organic

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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