Practical Methods for Biocatalysis and Biotransformations 2 (eBook, ePUB)

Redaktion: Whittall, John; Sutton, Peter W.

• Format: ePub

Produktbeschreibung

Biocatalysts are increasingly used by chemists engaged in fine chemical synthesis within both industry and academia. Today, there exists a huge choice of high-tech enzymes and whole cell biocatalysts, which add enormously to the repertoire of synthetic possibilities. Practical Methods for Biocatalysis and Biotransformations 2 is a "how-to" guide that focuses on the practical applications of enzymes and strains of microorganisms that are readily obtained or derived from culture collections. The sources of starting materials and reagents, hints, tips and safety advice (where appropriate) are given to ensure, as far as possible, that the procedures are reproducible. Comparisons to alternative methodology are given and relevant references to the primary literature are cited. This second volume - which can be used on its own or in combination with the first volume - concentrates on new applications and new enzyme families reported since the first volume. Contents include: * introduction to recent developments and future needs in biocatalysts and synthetic biology in industry * reductive amination * enoate reductases for reduction of electron deficient alkenes * industrial carbonyl reduction * regio- and stereo- selective hydroxylation * oxidation of alcohols * selective oxidation * industrial hydrolases and related enzymes * transferases for alkylation, glycosylation and phosphorylation * C-C bond formation and decarboxylation * halogenation/dehalogenation/heteroatom oxidation * tandem and sequential multi-enzymatic syntheses Practical Methods for Biocatalysis and Biotransformations 2 is an essential collection of biocatalytic methods for chemical synthesis which will find a place on the bookshelves of synthetic organic chemists, pharmaceutical chemists, and process R&D chemists in industry and academia.

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Produktdetails

• Verlag: John Wiley & Sons
• Seitenzahl: 368
• Erscheinungstermin: 25. April 2012
• Englisch
• ISBN-13: 9781118307861
• Artikelnr.: 37346534

Autorenporträt

John Whittall, Manchester Interdisciplinary Biocentre, Manchester University, UK. Peter W Sutton, GlaxoSmithKline Research and Development Limited, UK.

Inhaltsangabe

List of Contributors ix
Abbreviations xxiii
1 Biocatalysis in the Fine Chemical and Pharmaceutical Industries 1
1.1 Introduction 1
1.2 Biotrans Outsourcing - AstraZeneca 4
1.3 Biotrans Trends - Lonza 5
1.4 Biocatalysis in the Pharma Environment 9
1.5 Industrial Use of Hydrolases 24
1.6 Industrial Biooxidation and Reduction 32
1.7 Industrial Application of Transaminases - Cambrex 36
1.8 Biocatalyst Discovery and Improvement 38
1.9 From Pathway Engineering to Synthetic Biology 42
1.10 Prioritization of Future Biocatalysis and Synthetic Biology Needs 47
1.11 Concluding Remarks 52
2 Reductive Amination 61
2.1 o-Transaminases - Useful Biocatalysts for Chiral Amine Synthesis 61
2.2 Preparative Scale Production of a Bulky-Bulky Chiral Amine Using an
Engineered Transaminase 64
2.3 Synthesis of Optically Pure Amines Employing o-Transaminases 69
2.4 A Fast, Sensitive Assay and Scale-Up of o-Transaminase Catalysed
Reactions 74
2.5 Asymmetric Synthesis of L-3-Hydroxyadamantylglycine Using Branched
Chain Aminotransferase 79
2.6 Asymmetric Reduction of Aryl Imines Using Candida parapsilosis ATCC
7330 83
3 Enoate Reductases for Reduction of Electron Deficient Alkenes 87
3.1 Asymmetric Bioreduction of Activated Alkenes Using Ene-Reductases from
the Old Yellow Enzyme Family 87
3.2 Efficient Baker's Yeast Mediated Reduction with Substrate Feeding
Product Removal (SFPR) Technology: Synthesis of
(S)-2-Alkoxy-3-Aryl-1-Propanols 96
3.3 Asymmetric Reduction of (4S)-(+)-Carvone Catalyzed by Enoate Reductases
(ERs) Expressed by Non-Conventional Yeast (NCY) Whole Cells 100
3.4 Preparation of Enantiomerically Pure Citronellal Enantiomers Using
Alkene Reductases 104
3.5 Highly Enantiomeric Hydrogenation of C-C Double Bond of Methylated
N-Phenyl and N-Phenylalkylmaleimides by Aspergillus fumigatus 108
4 Industrial Carbonyl Reduction 115
4.1 Bioreduction Using Immobilized Carbonyl Reductase Technology 116
4.2 Preparative Ketoreductase-Catalyzed Kinetic Resolution of a Racemic
Aldehyde 118
4.3 Enzymatic Reduction of 2,6-dichloro-3-fluoro-acetophenone to Produce
(S)-1-(2,6-dichloro-3-fluorophenyl)ethanol 121
4.4 Preparative Scale Production of Poorly Soluble Chiral Alcohol
Intermediate for Montelukast 124
5 Regio- and Stereoselective Hydroxylation 129
5.1 Engineering of an Amycolatopsis orientalis P450 Compactin Hydroxylase
into a Pravastatin Synthase by Changing the Stereospecificity of the Enzyme
130
5.2 Recombinant Human Cytochrome P450 Enzymes Expressed in Escherichia coli
as Whole Cell Biocatalysts: Preparative Synthesis of Oxidized Metabolites
of an mGlu5 Receptor Antagonist 138
5.3 Alpha-Keto Biooxidation Using Cunninghamella echinulata (DSM 63356) 147
5.4 Aromatic Hydroxylation: Preparation of 3,4-Dihydroxyphenylacetic Acid
150
5.5 Regioselective Aromatic Hydroxylation of Quinaldine Using Living
Pseudomonas putida Cells Containing Quinaldine 4-Oxidase 153
5.6 Regioselective Preparation of 5-Hydroxypropranolol with a Fungal
Peroxygenase 158
5.7 Microbial Conversion of b-Myrcene to Geraniol by a Strain of
Rhodococcus 159
6 Oxidation of Alcohols 163
6.1 Preparative Method for the Enzymatic Synthesis of 5-Ketogluconic Acid
and its Isolation 163
6.2 Selective Enzymatic Oxidation of Atropisomeric Diaryl Ethers by
Oxidation with Oxygen and Catalytic Galactose Oxidase M3-5 166
6.3 Kinetic Resolution of Chiral Secondary Alcohols by Oxidation with
Oxygen and Catalytic Galactose Oxidase M3-5 169
6.4 ADH Catalyzed Oxidation of Sec-Alcohols Using Molecular Oxygen 172
6.5 Irreversible Non-Enantioselective Oxidation of Secondary Alcohols Using
Sphingobium ADH and Chloroacetone as Oxidant 175
6.6 Chemoselective Oxidation of Primary Alcohols to Aldehydes 177
7 Selective Oxidation 181
7.1 Enantioselective Biocatalytic Oxidative Desymmetrization of Substituted
Pyrrolidines 182
7.2 Large Scale Baeyer-Villiger Monooxygenase-Catalyzed Conversion of
(R,S)-3-phenylbutan-2-one 186
7.3 Synthesis of Optically Active 3-Alkyl-3-,4-dihydroioscoumarins by
Dynamic Kinetic Resolutions Catalyzed by a Baeyer-Villiger Monooxygenase
190
7.4 Oxidative Cleavage of the B-Ring of (+)-Catechin 193
7.5 18O-Isotopic Labeling in the Meta-Dioxygenase Cleavage of (þ)-Catechin
B-Ring 196
7.6 Biocatalytic Cleavage of Alkenes with Oxygen and Trametes hirsuta G
FCC047 199
8 Industrial Hydrolases and Related Enzymes 203
8.1 Dynamic Kinetic Resolution of a-Halo Esters with Hydrolytic Enzymes and
Sec-amine Bases 203
8.2 Kinetic Resolution of an Amino Ester Using Supported Mucor miehei
Lipase (Lipozyme RM IM) 207
8.3 Large Scale Synthesis of (S)-Allysine Ethylene Acetal via Amino Acylase
Resolution 212
8.4 Pilot-Scale Synthesis of (1R,2S,4S)-7-Oxabicyclo[2.2.1]
heptan-2-exo-carboxylic Acid 214
8.5 A Selective Lipase-Catalyzed Mono-Acetylation of a Diol Suitable for a
Telescoped Synthetic Process 217
8.6 A Protease-Mediated Hydrolytic Kinetic Resolution of an Atropisomeric
Ester Operating Within an Unusually Narrow pH Window 220
8.7 Asymmetric Synthesis of Quaternary Amino Acids from Simple Bis Nitriles
Using a Dual Nitrile Hydratase/Amidase Biocatalyzed Reaction 223
8.8 Development of an Improved Immobilized CAL-B for the Enzymatic
Resolution of a Key Intermediate to Odanacatib 227
9 Transferases for Alkylation, Glycosylation and Phosphorylation 231
9.1 Industrial Production of Caffeic Acid-a-D-O-Glucoside 232
9.2 Enzymatic Synthesis of 5-Methyluridine by Transglycosylation of
Guanosine and Thymine 235
9.3 Preparation and Use of Sucrose Phosphorylase as Cross-Linked Enzyme
Aggregate (CLEA) 240
9.4 Enzymatic Synthesis of Phosphorylated Carbohydrates and Alcohols 244
9.5 Biocatalyzed Synthesis of Chiral O-Phosphorylated Derivative of
2-Hydroxy-2-phenylethanephosphonate 247
9.6 High Activity b-Galactosidase Preparation for Diastereoselective
Synthesis of (R)-(1-Phenylethyl)-b-D-Galactopyranoside by Reverse
Hydrolysis 250
9.7 Stereospecific Synthesis of Aszonalenins by Using Two Recombinant
Prenyltransferases 254
9.8 Enzymatic Friedel-Crafts Alkylation Catalyzed by
S-Adenosyl-L-methionine Dependent Methyl Transferase 258
10 C-C Bond Formation and Decarboxylation 263
10.1 Enzymatic, Stereoselective Synthesis of (S)-Norcoclaurine 264
10.2 Preparation of Non-Natural Tyrosine Derivatives from Pyruvate and
Phenol Derivatives 267
10.3 Enzymatic a-Decarboxylation of L-Glutamic Acid in the Production of
Biobased Chemicals 269
10.4 Asymmetric Decarboxylation of Arylmalonates and Racemization of
Profens by Arylmalonate Decarboxylase and its Variants 274
10.5 Improved Enzymatic Preparation of 1-Deoxy-D-xylulose 5-Phosphate 280
10.6 On the Use of 2-Methyltetrahydrofuran (2-MeTHF) as Bio-Based (Co-)
Solvent in Biotransformations 284
10.7 The Lipase-Catalyzed Asymmetric Michael Addition of Thienyl
Nitroolefin to Acetylacetone 291
11 Halogenation/Dehalogenation/Heteroatom Oxidation 297
11.1 Preparation of Halogenated Molecules by a Fungal Flavin-Dependent
Halogenase Heterologously Expressed in Escherichia coli 299
11.2 Preparation of Optically Pure Haloalkanes and Alcohols by Kinetic
Resolution Using Haloalkane Dehalogenases 301
11.3 Preparation of Enantiopure Sulfoxides by Enantioselective Oxidation
with Whole Cells of Rhodococcus sp. ECU0066 307
11.4 Kinetic Resolution of an Insecticidal Dithiophosphate by
Chloroperoxidase Catalyzed Oxidation of the Thiophosphoryl Group 310
12 Tandem and Sequential Multi-Enzymatic Syntheses 313
12.1 Production of Isorhamnetin 3-O-Glucoside in Escherichia coli Using
Engineered Glycosyltransferase 313
12.2 Multienzymatic Preparation of (-)-3-(Oxiran-2-yl)Benzoic Acid 317
12.3 Enzymatic Synthesis of Carbohydrates from Dihydroxyacetone and
Aldehydes by a One Pot Enzyme Cascade Reaction 321
12.4 Aldolase Based Multi-Enzyme System for Carbon-Carbon Bond Formation
323
12.5 Tandem Biocatalytic Process for the Kinetic Resolution of
b-Phenylalanine and its Analogs 331
12.6 A Chemoenzymatic Synthesis of a Deoxy Sugar Ester of N-Boc-Protected
L-Tyrosine 335
12.7 Electrochemical Systems for the Recovery of Succinic Acid from
Fermentations 339
Appendix 347
Index 355