Practical Methods for Biocatalysis and Biotransformations

by Whittall, John; Sutton, Peter W.

• ISBN13: 9780470519271
• ISBN10: 0470519274
• Edition: 1st
• Format: Hardcover
• Copyright: 2009-12-30
• Publisher: Wiley

Summary

Practical Methods for Biocatalysis and Biotransformations is a "how-to" guide focusing on commercially available enzymes and strains of microorganisms that are readily obtained from culture collections. The source 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. Practical Methods for Biocatalysis and Biotransformations is an essential text offering validated biocatalyst methods for researchers and postgraduate students in industry and academia.

Author Biography

John Whittall

CoEBio3, Manchester Interdisciplinary Biocentre, Manchester University, UK

Peter W Sutton

GlaxoSmithKline Research and Development Limited, UK

Table of Contents

Preface

Abbreviations

Perspectives of Biotransformations in Small Molecule Pharmaceutical Development

Biocatalyst Identification and Scale-Up: Molecular Biology For Chemists

Kinetic Resolutions Using Biotransformations

Stereo- and enantioselective hydrolysis of rac-2-octylsulfate using whole resting cells of Pseudomonas spp

Protease-catalyzed resolutions using the 3-(3-pyridine)propionyl anchor group: p-toluenesulfonamide

Desymmetrisation of prochiral ketones using enzymes

Enzymatic Resolution of 1-Methyl-tetrahydroisoquinoline (1-MTQ) using Candida Rugosa Lipase

Dynamic Kinetic Resolution For the Synthesis of Esters, Amides and Acids Using Lipases

Dynamic Kinetic Resolution of 1-Phenylethanol by Immobilized Lipase Coupled with in-situ Racemization over Zeolite Beta

Synthesis of the (R)-butyrate esters of secondary alcohols by dynamic kinetic resolution employing a bis(Tetrafluorosuccinato)-Bridged Ru(II) Complex

Dynamic Kinetic Resolution of 6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline

Dynamic Kinetic Resolution of Primary Amines with a Recyclable Palladium Nanocatalyst (Pd /AlO(OH)) for Racemization

Dynamic Kinetic Resolution of Amines Involving Biocatalysis and in situ Free-Radical-Mediated Racemization

Chemoenzymatic Dynamic Kinetic Resolution of (S)-Ibuprofen

Dynamic kinetic resolution synthesis of a fluorinated amino acid ester amide by a continuous process lipase-mediated ethanolysis of an azalactone

Enzymatic Selectivity in Synthetic Methods

Alcalase Catalyzed Syntheses of Hydrophilic Di- and Tri-peptides in Organic Solvents

Selective alkoxycarbonylation of 1a,25-dihydroxyvitamin D₃ diol precursor with Candida antarctica lipase B

The use of lipase enzymes for the synthesis of polymers and polymer intermediates

Bioconversion of t3-cyanopyridine to nicotinic acid with Gordona terrae NDB1165

Enzyme-promoted desymmetrization of prochiral dinitriles

Epoxide Hydrolase Catalyzed Synthesis of (R)-3-benzyloxy-2-methylpropane-1,2-diol

One-pot biocatalytic synthesis of methyl (S)-4-chloro-3-hydroxybutanoate and methyl (S)-4-cyano-3-hydroxybutanoate Maja Majeric

Aldolase Enzymes For Complex Synthesis

One step synthesis of L-fructose using rhamnulose-1-phosphate aldolase in borate buffer

Straightforward Fructose-1,6-Diphosphate Aldolase mediated synthesis of aminocyclitols

Synthesis of D-fagomine by aldol addition of dihydroxyacetone to N-Cbz-3-aminopropanal catalyzed byD-fructose-6-phosphate aldolase José

Chemoenzymatic Synthesis of 5-Thio-D-Xylopyranose

Enzymatic Synthesis of Glycosides and Glucuronides

Glycosynthase-assisted Oligosaccharide Synthesis

Glycosyl Azides - Novel Substrates for Enzymatic Transglycosylations

Facile synthesis of alkyl ß-D-glucopyranosides from D-glucose and the corresponding alcohols using fruit seed meals

Laccase-Mediated Oxidation of Natural Glycosides

Biocatalyzed synthesis of monoglucuronides of Hydroxytyrosol, Tyrosol, Homovanillic Alcohol, and 3-(4'-Hydroxyphenyl)propanol using liver cells microsomal fractions

Synthesis of the acyl glucuronide of mycophenolic acid

Synthesis of Cyanohydrins Using Hydroxynitrile Lyases

Synthesis of (S)-2-Hydroxy-2-methylbutyric Acid by a Chemoenzymatic Methodology

(S)-Selective cyanohydrin synthesis from aromatic ketones using hydroxynitrile lyases

Hydroxynitrile lyase catalysed synthesis of enantiopure (S)-acetophenone cyanohydrins

(R)- and (S)-Cyanohydrin synthesis from pyridine-3-carboxaldehyde using CLEA-immobilized hydroxynitrile lyases

A new (R)-Hydroxynitrile lyase from Prunus mume for Asymmetric Synthesis of Cyanohydrins

Synthesis of Chiral Sec-Alcohols by Ketone Reduction

Asymmetric synthesis (S)-bis-(trifluoromethyl)phenyl ethanol by biocatalytic reduction of bis-(trifluoromethyl)acetophenone

Enantioselective and diastereoselective enzyme-catalyzed dynamic kinetic resolution of an unsaturated ketone

Enzyme-catalyzed synthesis of a-alkyl-b-hydroxy ketones and esters by isolated ketoreductases

Asymmetric reduction of phenyl ring-containing ketones using xerogel-encapsulated W110A secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus

(R)- and (S)- Enantioselective diaryl methanol synthesis using enzymatic reduction of diaryl ketones

Highly enantioselective and efficient synthesis of methyl (R)-o-chloromandelate, key intermediate for clopidogrel, with recombinant E. coli

Reduction of Functional Groups

Reduction of Carboxylic Acids by Carboxylic Acid Reductase (Car) heterologously expressed in E. coli

Light-driven Stereoselective Biocatalytic Oxidations and Reductions

Unnatural amino acids by enzymatic transamination: synthesis of glutamic acid analogues with aspartate aminotransferase

Synthesis of L-Pipecolic Acid with D¹-Piperidine-2-carboxylate Reductase from Pseudomonas putida Hisaaki Mihara and Nobuyoshi Esaki

Synthesis of substituted derivatives of L-phenylalanine and of other non-natural L-amino acids using engineered mutants of phenylalanine dehydrogenase

Enzymatic Oxidation Chemistry

Monoamine Oxidase (MAO-N) Catalysed Reactions: Application Towards the Chemo-Enzymatic Deracemisation of the Alkaloid (±)-Crispine A

Glucose oxidase catalysed synthesis of aldonic acids

Oxidation and halo-hydroxylation of monoterpenes with chloroperoxidase from Caldariomyces fumago

Chloroperoxidase (CPO) Catalyzed Oxidation of Phenyl Methylsulfide in Ionic Liquids

Stereoselective synthesis of b-hydroxy sulfoxides catalyzed by cyclohexanone monooxygenase

Enantioselective kinetic resolution of racemic 3-phenylbutan-2-one using a Baeyer-Villiger monooxygenase

Desymmetrisation of 1-methylbicyclo[3.3.0]octane-2,8-dione by the retro-Claisenase 6-oxo camphor hydrolase

Synthesis of optically pure chiral lactones by cyclopentadecanone monooxygenase (CPDMO)-catalyzed Baeyer-Villiger oxidations

Whole Cell Oxidations and Dehalogenations

Biotransformations of naphthalene to 4-hydroxy-1-tetralone by Streptomyces griseus NRRL 8090

Hydroxylation of imidacloprid for the synthesis of olefin imidacloprid by Stenotrophomonas maltophilia CGMCC 1.1788

Biocatalytic synthesis of 6-hydroxy fluvastatin using Motierella rammaniana DSM 62752 in shake flask culture and on multi-gram scale using a Wave bioreactor

Synthesis of 1-adamantanol from adamantane through regioselective hydroxylation by Streptomyces griseoplanus cells

Enantioselective benzylic microbial hydroxylation of indan and tetralin

Stereospecific biotransformation of (R/S)-linalool by Corynespora cassiicola DSM 62475 into linalool oxides

The biocatalytic synthesis of 4-fluorocatechol from fluorobenzene

Synthesis of enantiopure (S)-styrene oxide by selective oxidation of styrene by recombinant E.coli JM101 (pSPZ10)

Biotransformation of a-bromo- and a,a'-dibromo alkanone into a-hydroxyketone and a-diketone by Spirulina platensis

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