Title:
Practical methods for biocatalysis and biotransformations
Publication Information:
Chichester, UK : J. Wiley, 2010
Physical Description:
xxix, 402 p. : ill. ; 25 cm.
ISBN:
9780470519271
Available:*
Library | Item Barcode | Call Number | Material Type | Item Category 1 | Status |
|---|---|---|---|---|---|
Searching... | 30000010236352 | TP248.65.E59 P72 2010 | Open Access Book | Book | Searching... |
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Summary
Summary
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 is a "how-to" guide focussing 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. Contents include:
Introduction to the application of biocatalysts in the pharma industry introduction to molecular biological techniques for biocatalyst development Lipase and protease methods including enzyme supports and dynamic kinetic resolutions Nitrile hydrolases and hydratases Alcohol dehydrogenases and co-factor recycling Epoxide hydrolases Amino acid synthesis Whole cell processes Other biocatalysts, including monoamineoxidases, aminotransterases, and lyasesPractical Methods for Biocatalysis and Biotransformations is an essential text offering validated biocatalyst methods for researchers and postgraduate students in industry and academia.
Author Notes
John Whittall
CoEBio3, Manchester Interdisciplinary Biocentre, Manchester University, UK
Peter W Sutton
GlaxoSmithKline Research and Development Limited, UK
Table of Contents
| Preface |
| Abbreviations |
| Chapter 1 Perspectives of Biotransformations in Small Molecule Pharmaceutical DevelopmentJoseph P. Adams and Andrew J. Collis and Richard K. Henderson and Peter W. Sutton |
| Chapter 2 Biocatalyst Identification and Scale-Up: Molecular Biology For ChemistsKathleen.H.McClean |
| Chapter 3 Kinetic Resolutions Using Biotransformations |
| 3.1 Stereo- and enantioselective hydrolysis of rac-2-octylsulfate using whole resting cells of Pseudomonas sppPetra Gadler and Kurt Faber |
| 3.2 Protease-catalyzed resolutions using the 3-(3-pyridine)propionyl anchor group: p-toluenesulfonamideChristopher K. Savile and Romas J. Kazlauskas |
| 3.3 Desymmetrisation of prochiral ketones using enzymesAndrew J. Carnell |
| 3.4 Enzymatic Resolution of 1-Methyl-tetrahydroisoquinoline (1-MTQ) using Candida Rugosa LipaseGary Breen |
| Chapter 4 Dynamic Kinetic Resolution For the Synthesis of Esters, Amides and Acids Using Lipases |
| 4.1 Dynamic Kinetic Resolution of 1-Phenylethanol by Immobilized Lipase Coupled with in-situ Racemization over Zeolite BetaKam Loon Fow and Yongzhong Zhu and Gaik Khuan Chuah and Stephan Jaenicke |
| 4.2 Synthesis of the (R)-butyrate esters of secondary alcohols by dynamic kinetic resolution employing a bis(Tetrafluorosuccinato)-Bridged Ru(II) ComplexS.F.G.M. van Nispen and J. van Buijtenen and J.A.J.M. Vekemans and J. Meuldijk and L.A. Hulshof |
| 4.3 Dynamic Kinetic Resolution of 6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinolineMichael Page and John Blacker and Matthew Stirling |
| 4.4 Dynamic Kinetic Resolution of Primary Amines with a Recyclable Palladium Nanocatalyst (Pd /AlO(OH)) for RacemizationSoo-Byung Ko and Mahn-Joo Kim and Jaiwook Park |
| 4.5 Dynamic Kinetic Resolution of Amines Involving Biocatalysis and in situ Free-Radical-Mediated RacemizationStéphane Gastaldi and Gérard Gil and Michèle P. Bertrand |
| 4.6 Chemoenzymatic Dynamic Kinetic Resolution of (S)-IbuprofenA.H. Kamaruddin and F. Hamzah |
| 4.7 Dynamic kinetic resolution synthesis of a fluorinated amino acid ester amide by a continuous process lipase-mediated ethanolysis of an azalactoneMatthew Truppo and David Pollard and Jeffrey Moore and Paul Devine |
| Chapter 5 Enzymatic Selectivity in Synthetic Methods |
| 5.1 Alcalase Catalyzed Syntheses of Hydrophilic Di- and Tri-peptides in Organic SolventsXue-Zhong Zhang and Rui-Zhen Hou and Li Xu and Yi-Bing Huang |
| 5.2 Selective alkoxycarbonylation of 1a,25-dihydroxyvitamin D 3 diol precursor with Candida antarctica lipase BMiguel Ferrero and Susana Fernández and Vicente Gotor |
| 5.3 The use of lipase enzymes for the synthesis of polymers and polymer intermediatesAlan Taylor |
| 5.4 Bioconversion of t3-cyanopyridine to nicotinic acid with Gordona terrae NDB1165Tek Chand Bhalla |
| 5.5 Enzyme-promoted desymmetrization of prochiral dinitrilesMarloes A. Wijdeven and Piotr Kielbasinski and Floris P. J. T. Rutjes |
| 5.6 Epoxide Hydrolase Catalyzed Synthesis of (R)-3-benzyloxy-2-methylpropane-1,2-diolTakeshi Sugai and Aya Fujino |
| 5.7 One-pot biocatalytic synthesis of methyl (S)-4-chloro-3-hydroxybutanoate and methyl (S)-4-cyano-3-hydroxybutanoate Maja MajericElenkov and Lixia Tang and Bernhard Hauer and Dick B. Janssen |
| Chapter 6 Aldolase Enzymes For Complex Synthesis |
| 6.1 One step synthesis of L-fructose using rhamnulose-1-phosphate aldolase in borate bufferWilliam A. Greenberg and Chi-Huey Wong |
| 6.2 Straightforward Fructose-1,6-Diphosphate Aldolase mediated synthesis of aminocyclitolsMarielle Lemaire and Lahssen El Blidi |
| 6.3 Synthesis of D-fagomine by aldol addition of dihydroxyacetone to N-Cbz-3-aminopropanal catalyzed byD-fructose-6-phosphate aldolase JoséA. Castillo and Teodor Parella and Tomoyuki Inoue and Georg A. Sprenger and Jesús Joglar and Pere Clapés |
| 6.4 Chemoenzymatic Synthesis of 5-Thio-D-XylopyranoseFranck Charmantray and Philippe Dellis and Virgil Hélaine and Soth Samreth and Laurence Hecquet |
| Chapter 7 Enzymatic Synthesis of Glycosides and Glucuronides |
| 7.1 Glycosynthase-assisted Oligosaccharide SynthesisAdrian Scaffidi and Robert V Stick |
| 7.2 Glycosyl Azides - Novel Substrates for Enzymatic TransglycosylationsVladimír Kren and Pavla Bojarová |
| 7.3 Facile synthesis of alkyl ß-D-glucopyranosides from D-glucose and the corresponding alcohols using fruit seed mealsWen-Ya Lua and Guo-Qiang Lin and Hui-Lei Yub and Ai-Ming Tongb and Jian-He Xu |
| 7.4 Laccase-Mediated Oxidation of Natural GlycosidesCosimo Chirivì and Francesca Sagui and Sergio Riva |
| 7.5 Biocatalyzed synthesis of monoglucuronides of Hydroxytyrosol, Tyrosol, Homovanillic Alcohol, and 3-(4'-Hydroxyphenyl)propanol using liver cells microsomal fractionsOlha Khymenets and Pere Clapés and Teodor Parella and María-Isabel Covas and Rafael de la Torre and Jesús Joglar |
| 7.6 Synthesis of the acyl glucuronide of mycophenolic acidMatthias Kittelmann and Lukas Oberer and Reiner Aichholz and Oreste Ghisalba |
| Chapter 8 Synthesis of Cyanohydrins Using Hydroxynitrile Lyases |
| 8.1 Synthesis of (S)-2-Hydroxy-2-methylbutyric Acid by a Chemoenzymatic MethodologyManuela Avi and Herfried Griengl |
| 8.2 (S)-Selective cyanohydrin synthesis from aromatic ketones using hydroxynitrile lyasesChris Roberge and Fred Fleitz and Paul Devine |
| 8.3 Hydroxynitrile lyase catalysed synthesis of enantiopure (S)-acetophenone cyanohydrinsJan von Langermann and Annett Mell and Eckhard Paetzold and Udo Kragl |
| 8.4 (R)- and (S)-Cyanohydrin synthesis from pyridine-3-carboxaldehyde using CLEA-immobilized hydroxynitrile lyasesChris Roberge and Fred Fleitz and Paul Devine |
| 8.5 A new (R)-Hydroxynitrile lyase from Prunus mume for Asymmetric Synthesis of CyanohydrinsYasuhisa Asano |
| Chapter 9 Synthesis of Chiral Sec-Alcohols by Ketone Reduction |
| 9.1 Asymmetric synthesis (S)-bis-(trifluoromethyl)phenyl ethanol by biocatalytic reduction of bis-(trifluoromethyl)acetophenoneDavid Pollard and Matthew Truppo and Jeffrey Moore |
| 9.2 Enantioselective and diastereoselective enzyme-catalyzed dynamic kinetic resolution of an unsaturated ketoneBirgit Kosjek and David Tellers and Jeffrey Moore |
| 9.3 Enzyme-catalyzed synthesis of a-alkyl-b-hydroxy ketones and esters by isolated ketoreductasesIoulia Smonou and Dimitris Kalaitzakis |
| 9.4 Asymmetric reduction of phenyl ring-containing ketones using xerogel-encapsulated W110A secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicusMusa M. Musa and Karla I. Ziegelmann-Fjeld and Claire Vieille and J. Gregory Zeikus and Robert S. Phillips |
| 9.5 (R)- and (S)- Enantioselective diaryl methanol synthesis using enzymatic reduction of diaryl ketonesMatthew Truppo and Krista Morley and David Pollard and Paul Devine |
| 9.6 Highly enantioselective and efficient synthesis of methyl (R)-o-chloromandelate, key intermediate for clopidogrel, with recombinant E. coliTadashi Ema and Nobuyasu Okita and Sayaka Ide and Takashi Sakai |
| Chapter 10 Reduction of Functional Groups |
| 10.1 Reduction of Carboxylic Acids by Carboxylic Acid Reductase (Car) heterologously expressed in E. coliAndrew S. Lamm and Arshdeep Khare and John P. N. Rosazza |
| 10.2 Light-driven Stereoselective Biocatalytic Oxidations and ReductionsAndreas Taglieber and Frank Schulz and Frank Hollmann and Monika Rusek and Manfred T. Reetz |
| 10.3 Unnatural amino acids by enzymatic transamination: synthesis of glutamic acid analogues with aspartate aminotransferaseThierry Gefflaut and Emmanuelle Sagot and Jean Bolte |
| 10.4 Synthesis of L-Pipecolic Acid with D 1 -Piperidine-2-carboxylate Reductase from Pseudomonas putida Hisaaki Mihara and Nobuyoshi Esaki |
| 10.5 Synthesis of substituted derivatives of L-phenylalanine and of other non-natural L-amino acids using engineered mutants of phenylalanine dehydrogenasePhilip Conway and Francesca Paradisi and Paul Engel |
| Chapter 11 Enzymatic Oxidation Chemistry |
| 11.1 Monoamine Oxidase (MAO-N) Catalysed Reactions: Application Towards the Chemo-Enzymatic Deracemisation of the Alkaloid (±)-Crispine AAndrew J. Ellis and Renate Reiss and Timothy J. Snape and Nicholas J. Turner |
| 11.2 Glucose oxidase catalysed synthesis of aldonic acidsFabio Pezzotti and Helene Therisod and Michel Therisod |
| 11.3 Oxidation and halo-hydroxylation of monoterpenes with chloroperoxidase from Caldariomyces fumagoBjoern-Arne Kaup and Jens Schrader |
| 11.4 Chloroperoxidase (CPO) Catalyzed Oxidation of Phenyl Methylsulfide in Ionic LiquidsCinzia Chiappe |
| 11.5 Stereoselective synthesis of b-hydroxy sulfoxides catalyzed by cyclohexanone monooxygenaseStefano Colonna and Nicoletta Gaggero and Sara Pellegrino and Francesca Zambianchi |
| 11.6 Enantioselective kinetic resolution of racemic 3-phenylbutan-2-one using a Baeyer-Villiger monooxygenaseAnett Kirschner and Uwe T. Bornscheuer |
| 11.7 Desymmetrisation of 1-methylbicyclo[3.3.0]octane-2,8-dione by the retro-Claisenase 6-oxo camphor hydrolaseGideon Grogan and Cheryl Hill |
| 11.8 Synthesis of optically pure chiral lactones by cyclopentadecanone monooxygenase (CPDMO)-catalyzed Baeyer-Villiger oxidationsShaozhao Wang and Jianzhong Yang and Peter C.K. Lau |
| Chapter 12 Whole Cell Oxidations and Dehalogenations |
| 12.1 Biotransformations of naphthalene to 4-hydroxy-1-tetralone by Streptomyces griseus NRRL 8090Arshdeep Khare and Andrew S. Lamm and John P. N. Rosazza |
| 12.2 Hydroxylation of imidacloprid for the synthesis of olefin imidacloprid by Stenotrophomonas maltophilia CGMCC 1.1788Sheng Yuan and Yi-jun Dai |
| 12.3 Biocatalytic synthesis of 6-hydroxy fluvastatin using Motierella rammaniana DSM 62752 in shake flask culture and on multi-gram scale using a Wave bioreactorMatthias Kittelmann and Maria Serrano Correia and Anton Kuhn and Serge Parel and Jürgen Kühnöl and Reiner Aichholz and Monique Ponelle and Oreste Ghisalba |
| 12.4 Synthesis of 1-adamantanol from adamantane through regioselective hydroxylation by Streptomyces griseoplanus cellsKoichi Mitsukura and Yoshinori Kondo and Toyokazu Yoshida and Toru Nagasawa |
| 12.5 Enantioselective benzylic microbial hydroxylation of indan and tetralinRenata P. Limberger and Cleber V. Ursini and Paulo J. S. Moran and J. Augusto R. Rodrigues |
| 12.6 Stereospecific biotransformation of (R/S)-linalool by Corynespora cassiicola DSM 62475 into linalool oxidesMarco-Antonio Mirata and Jens Schrader |
| 12.7 The biocatalytic synthesis of 4-fluorocatechol from fluorobenzeneLouise C. Nolan and Kevin E. O' Connor |
| 12.8 Synthesis of enantiopure (S)-styrene oxide by selective oxidation of styrene by recombinant E.coli JM101 (pSPZ10)Katja Otto and Andreas Schmid |
| 12.9 Biotransformation of a-bromo- and a,a'-dibromo alkanone into a-hydroxyketone and a-diketone by Spirulina platensisTakamitsu Utsukihara and C. Akira Horiuchi |
