PRACTICAL METHODS FOR BIOCATALYSIS AND BIOTRANSFORMATIONS 2 -- Contents -- List of Contributors -- Abbreviations -- 1 Biocatalysis in the Fine Chemical and Pharmaceutical Industries -- 1.1 Introduction -- 1.2 Biotrans Outsourcing - AstraZeneca -- 1.3 Biotrans Trends - Lonza -- 1.4 Biocatalysis in the Pharma Environment -- 1.5 Industrial Use of Hydrolases -- 1.6 Industrial Biooxidation and Reduction -- 1.7 Industrial Application of Transaminases - Cambrex -- 1.8 Biocatalyst Discovery and Improvement -- 1.9 From Pathway Engineering to Synthetic Biology -- 1.10 Prioritization of Future Biocatalysis and Synthetic Biology Needs -- 1.11 Concluding Remarks -- Acknowledgements -- References -- 2 Reductive Amination -- 2.1 ω-Transaminases - Useful Biocatalysts for Chiral Amine Synthesis -- 2.2 Preparative Scale Production of a Bulky-Bulky Chiral Amine Using an Engineered Transaminase -- 2.3 Synthesis of Optically Pure Amines Employing ω-Transaminases -- 2.4 A Fast, Sensitive Assay and Scale-Up of ω-Transaminase Catalysed Reactions -- 2.5 Asymmetric Synthesis of L-3-Hydroxyadamantylglycine Using Branched Chain Aminotransferase -- 2.6 Asymmetric Reduction of Aryl Imines Using Candida parapsilosis ATCC 7330 -- 3 Enoate Reductases for Reduction of Electron Deficient Alkenes -- 3.1 Asymmetric Bioreduction of Activated Alkenes Using Ene-Reductases from the Old Yellow Enzyme Family -- 3.2 Efficient Baker's Yeast Mediated Reduction with Substrate Feeding Product Removal (SFPR) Technology: Synthesis of (S)-2-Alkoxy-3-Aryl-1-Propanols -- 3.3 Asymmetric Reduction of (4S)-(+)-Carvone Catalyzed by Enoate Reductases (ERs) Expressed by Non-Conventional Yeast (NCY) Whole Cells -- 3.4 Preparation of Enantiomerically Pure Citronellal Enantiomers Using Alkene Reductases.

3.5 Highly Enantiomeric Hydrogenation of C-C Double Bond of Methylated N-Phenyl and N-Phenylalkylmaleimides by Aspergillus fumigatus -- 4 Industrial Carbonyl Reduction -- 4.1 Bioreduction Using Immobilized Carbonyl Reductase Technology -- 4.2 Preparative Ketoreductase-Catalyzed Kinetic Resolution of a Racemic Aldehyde -- 4.3 Enzymatic Reduction of 2,6-dichloro-3-fluoro-acetophenone to Produce (S)-1-(2,6-dichloro-3-fluorophenyl)ethanol -- 4.4 Preparative Scale Production of Poorly Soluble Chiral Alcohol Intermediate for Montelukast -- 5 Regio- and Stereoselective Hydroxylation -- 5.1 Engineering of an Amycolatopsis orientalis P450 Compactin Hydroxylase into a Pravastatin Synthase by Changing the Stereospecificity of the Enzyme -- 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 -- 5.3 Alpha-Keto Biooxidation Using Cunninghamella echinulata (DSM 63356) -- 5.4 Aromatic Hydroxylation: Preparation of 3,4-Dihydroxyphenylacetic Acid -- 5.5 Regioselective Aromatic Hydroxylation of Quinaldine Using Living Pseudomonas putida Cells Containing Quinaldine 4-Oxidase -- 5.6 Regioselective Preparation of 5-Hydroxypropranolol with a Fungal Peroxygenase -- 5.7 Microbial Conversion of β-Myrcene to Geraniol by a Strain of Rhodococcus -- 6 Oxidation of Alcohols -- 6.1 Preparative Method for the Enzymatic Synthesis of 5-Ketogluconic Acid and its Isolation -- 6.2 Selective Enzymatic Oxidation of Atropisomeric Diaryl Ethers by Oxidation with Oxygen and Catalytic Galactose Oxidase M3-5 -- 6.3 Kinetic Resolution of Chiral Secondary Alcohols by Oxidation with Oxygen and Catalytic Galactose Oxidase M3-5 -- 6.4 ADH Catalyzed Oxidation of Sec-Alcohols Using Molecular Oxygen.

6.5 Irreversible Non-Enantioselective Oxidation of Secondary Alcohols Using Sphingobium ADH and Chloroacetone as Oxidant -- 6.6 Chemoselective Oxidation of Primary Alcohols to Aldehydes -- 7 Selective Oxidation -- 7.1 Enantioselective Biocatalytic Oxidative Desymmetrization of Substituted Pyrrolidines -- 7.2 Large Scale Baeyer-Villiger Monooxygenase-Catalyzed Conversion of (R,S)-3-phenylbutan-2-one -- 7.3 Synthesis of Optically Active 3-Alkyl-3-,4-dihydroioscoumarins by Dynamic Kinetic Resolutions Catalyzed by a Baeyer-Villiger Monooxygenase -- 7.4 Oxidative Cleavage of the B-Ring of (+)-Catechin -- 7.5 18O-Isotopic Labeling in the Meta-Dioxygenase Cleavage of (+)-Catechin B-Ring -- 7.6 Biocatalytic Cleavage of Alkenes with Oxygen and Trametes hirsuta G FCC047 -- 8 Industrial Hydrolases and Related Enzymes -- 8.1 Dynamic Kinetic Resolution of α-Halo Esters with Hydrolytic Enzymes and Sec-amine Bases -- 8.2 Kinetic Resolution of an Amino Ester Using Supported Mucor miehei Lipase (Lipozyme® RM IM) -- 8.3 Large Scale Synthesis of (S)-Allysine Ethylene Acetal via Amino Acylase Resolution -- 8.4 Pilot-Scale Synthesis of (1R,2S,4S)-7-Oxabicyclo[2.2.1] heptan-2-exo-carboxylic Acid -- 8.5 A Selective Lipase-Catalyzed Mono-Acetylation of a Diol Suitable for a Telescoped Synthetic Process -- 8.6 A Protease-Mediated Hydrolytic Kinetic Resolution of an Atropisomeric Ester Operating Within an Unusually Narrow pH Window -- 8.7 Asymmetric Synthesis of Quaternary Amino Acids from Simple Bis Nitriles Using a Dual Nitrile Hydratase/Amidase Biocatalyzed Reaction -- 8.8 Development of an Improved Immobilized CAL-B for the Enzymatic Resolution of a Key Intermediate to Odanacatib -- 9 Transferases for Alkylation, Glycosylation and Phosphorylation -- 9.1 Industrial Production of Caffeic Acid-α-D-O-Glucoside.

9.2 Enzymatic Synthesis of 5-Methyluridine by Transglycosylation of Guanosine and Thymine -- 9.3 Preparation and Use of Sucrose Phosphorylase as Cross-Linked Enzyme Aggregate (CLEA) -- 9.4 Enzymatic Synthesis of Phosphorylated Carbohydrates and Alcohols -- 9.5 Biocatalyzed Synthesis of Chiral O-Phosphorylated Derivative of 2-Hydroxy-2-phenylethanephosphonate -- 9.6 High Activity β-Galactosidase Preparation for Diastereoselective Synthesis of (R)-(1-Phenylethyl)-β-D-Galactopyranoside by Reverse Hydrolysis -- 9.7 Stereospecific Synthesis of Aszonalenins by Using Two Recombinant Prenyltransferases -- 9.8 Enzymatic Friedel-Crafts Alkylation Catalyzed by S-Adenosyl- L-methionine Dependent Methyl Transferase -- 10 C-C Bond Formation and Decarboxylation -- 10.1 Enzymatic, Stereoselective Synthesis of (S)-Norcoclaurine -- 10.2 Preparation of Non-Natural Tyrosine Derivatives from Pyruvate and Phenol Derivatives -- 10.3 Enzymatic α-Decarboxylation of L-Glutamic Acid in the Production of Biobased Chemicals -- 10.4 Asymmetric Decarboxylation of Arylmalonates and Racemization of Profens by Arylmalonate Decarboxylase and its Variants -- 10.5 Improved Enzymatic Preparation of 1-Deoxy-D-xylulose 5-Phosphate -- 10.6 On the Use of 2-Methyltetrahydrofuran (2-MeTHF) as Bio-Based (Co-) Solvent in Biotransformations -- 10.7 The Lipase-Catalyzed Asymmetric Michael Addition of Thienyl Nitroolefin to Acetylacetone -- 11 Halogenation/Dehalogenation/Heteroatom Oxidation -- 11.1 Preparation of Halogenated Molecules by a Fungal Flavin- Dependent Halogenase Heterologously Expressed in Escherichia coli -- 11.2 Preparation of Optically Pure Haloalkanes and Alcohols by Kinetic Resolution Using Haloalkane Dehalogenases -- 11.3 Preparation of Enantiopure Sulfoxides by Enantioselective Oxidation with Whole Cells of Rhodococcus sp. ECU0066.

11.4 Kinetic Resolution of an Insecticidal Dithiophosphate by Chloroperoxidase Catalyzed Oxidation of the Thiophosphoryl Group -- 12 Tandem and Sequential Multi-Enzymatic Syntheses -- 12.1 Production of Isorhamnetin 3-O-Glucoside in Escherichia coli Using Engineered Glycosyltransferase -- 12.2 Multienzymatic Preparation of (―)-3-(Oxiran-2-yl)Benzoic Acid -- 12.3 Enzymatic Synthesis of Carbohydrates from Dihydroxyacetone and Aldehydes by a One Pot Enzyme Cascade Reaction -- 12.4 Aldolase Based Multi-Enzyme System for Carbon-Carbon Bond Formation -- 12.5 Tandem Biocatalytic Process for the Kinetic Resolution of β-Phenylalanine and its Analogs -- 12.6 A Chemoenzymatic Synthesis of a Deoxy Sugar Ester of N-Boc-Protected L-Tyrosine -- 12.7 Electrochemical Systems for the Recovery of Succinic Acid from Fermentations -- Appendix -- Index.