ISBN-10:
0470519274
ISBN-13:
9780470519271
Pub. Date:
01/05/2010
Publisher:
Wiley
Practical Methods for Biocatalysis and Biotransformations / Edition 1

Practical Methods for Biocatalysis and Biotransformations / Edition 1

by John Whittall, Peter W. Sutton

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Overview

Practical Methods for Biocatalysis and Biotransformations / Edition 1

Biocatalysts are increasingly used by chemists engaged in finechemical synthesis within both industry and academia. Today, thereexists a huge choice of high-tech enzymes and whole cellbiocatalysts, which add enormously to the repertoire of syntheticpossibilities.

Practical Methods for Biocatalysis and Biotransformationsis a “how-to” guide focussing on commercially availableenzymes and strains of microorganisms that are readily obtainedfrom culture collections. The source of starting materials andreagents, hints, tips and safety advice (where appropriate) aregiven to ensure, as far as possible, that the procedures arereproducible. Comparisons to alternative methodology are given andrelevant references to the primary literature are cited. Contentsinclude:

  • Introduction to the application of biocatalysts in the pharmaindustry
  • introduction to molecular biological techniques for biocatalystdevelopment
  • Lipase and protease methods including enzyme supports anddynamic 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 lyases

Practical Methods for Biocatalysis and Biotransformationsis an essential text offering validated biocatalyst methods forresearchers and postgraduate students in industry and academia.

Product Details

ISBN-13: 9780470519271
Publisher: Wiley
Publication date: 01/05/2010
Pages: 432
Product dimensions: 6.80(w) x 9.80(h) x 1.10(d)

About the Author

John Whittall

CoEBio3, Manchester Interdisciplinary Biocentre, ManchesterUniversity, UK

Peter W Sutton

GlaxoSmithKline Research and Development Limited, UK

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Table of Contents

Preface.

Abbreviations.

List of Contributors.

1 Biotransformations in Small-molecule PharmaceuticalDevelopment (Joseph P. Adams, Andrew J. Collis, Richard K.Henderson and Peter W. Sutton).

2 Biocatalyst Identification and Scale-up: Molecular Biology forChemists (Kathleen H. McClean).

3 Kinetic Resolutions Using Biotransformations.

3.1 Stereo- and Enantio-selective Hydrolysis ofrac-2-Octylsulfate Using Whole Resting Cells of Pseudomonas spp.(Petra Gadler and Kurt Faber).

3.2 Protease-catalyzed Resolutions Using the3-(3-Pyridine)propionyl Anchor Group: p-Toluenesulfonamide(Christopher K. Savile and Romas J. Kazlauskas).

3.3 Desymmetrization of Prochiral Ketones Using Enzymes (AndrewJ. Carnell).

3.4 Enzymatic Resolution of 1-Methyl-tetrahydroisoquinolineusing Candida rugosa Lipase (Gary Breen).

4 Dynamic Kinetic Resolution for the Synthesis of Esters, Amidesand Acids Using Lipases.

4.1 Dynamic Kinetic Resolution of 1-Phenylethanol by ImmobilizedLipase Coupled with In Situ Racemization over Zeolite Beta (KamLoon Fow, Yongzhong Zhu, Gaik Khuan Chuah and StephanJaenicke).

4.2 Synthesis of the (R)-Butyrate Esters of Secondary Alcoholsby Dynamic Kinetic Resolution Employing aBis(tetrafluorosuccinato)-bridged Ru(II) Complex (S.F.G.M. vanNispen, J. van Buijtenen, J.A.J.M. Vekemans, J. Meuldijk and L.A.Hulshof).

4.3 Dynamic Kinetic Resolution6,7-Dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline (MichaelPage, John Blacker and Matthew Stirling).

4.4 Dynamic Kinetic Resolution of Primary Amines with aRecyclable Palladium Nanocatalyst (Pd/AlO(OH)) for Racemization(Soo-Byung Ko, Mahn-Joo Kim and Jaiwook Park).

4.5 Dynamic Kinetic Resolution of Amines Involving Biocatalysisand In Situ Free-radical-mediated Racemization (StéphaneGastaldi, Ge´rard Gil and Michèle P. Bertrand).

4.6 Chemoenzymatic Dynamic Kinetic Resolution of (S)-Ibuprofen(A.H. Kamaruddin and F. Hamzah).

4.7 Dynamic Kinetic Resolution Synthesis of a Fluorinated AminoAcid Ester Amide by a Continuous Process Lipase-mediatedEthanolysis of an Azalactone (Matthew Truppo, David Pollard,Jeffrey Moore and Paul Devine).

5 Enzymatic Selectivity in Synthetic Methods.

5.1 Alcalase-catalysed Syntheses of Hydrophilic Di- andTri-peptides in Organic Solvents (Xue-Zhong Zhang, Rui-Zhen Hou, LiXu and Yi-Bing Huang).

5.2 Selective Alkoxycarbonylation of 1,25-Dihydroxyvitamin D3Diol Precursor with Candida antarctica Lipase B (Miguel Ferrero,Susana Fernández and Vicente Gotor).

5.3 The Use of Lipase Enzymes for the Synthesis of Polymers andPolymer Intermediates (Alan Taylor).

5.4 Bioconversion of 3-Cyanopyridine into Nicotinic Acid withGordona terrae NDB1165 (Tek Chand Bhalla).

5.5 Enzyme-promoted Desymmetrization of Prochiral Dinitriles(Marloes A. Wijdeven, Piotr Kiełbasinski and FlorisP.J.T. Rutjes).

5.6 Epoxide Hydrolase-catalyzed Synthesis of(R)-3-Benzyloxy-2-methylpropane-1,2-diol (Takeshi Sugai, AyaFujino, Hitomi Yamaguchi and Masaya Ikunaka).

5.7 One-pot Biocatalytic Synthesis of Methyl(S)-4-Chloro-3-hydroxybutanoate and Methyl(S)-4-Cyano-3-hydroxybutanoate (Maja Majeric´ Elenkov, LixiaTang, Bernhard Hauer and Dick B. Janssen).

6 Aldolase Enzymes for Complex Synthesis.

6.1 One-step Synthesis of L-Fructose UsingRhamnulose-1-phosphate Aldolase in Borate Buffer (William A.Greenberg and Chi-Huey Wong).

6.2 Straightforward Fructose-1,6-bisphosphate Aldolase-mediatedSynthesis of Aminocyclitols (Marielle Lemaire and Lahssen ElBlidi).

6.3 Synthesis of D-Fagomine by Aldol Addition ofDihydroxyacetone to N-Cbz-3-AminopropanalCatalysedbyD-Fructose-6-phosphateAldolase (José A. Castillo,Teodor Parella, Tomoyuki Inoue, Georg A. Sprenger, JesusJoglar and Pere Clapés).

6.4 Chemoenzymatic Synthesis of 5-Thio-D-xylopyranose (FranckCharmantray, Philippe Dellis, Virgil He´laine, Soth Samrethand Laurence Hecquet).

7 Enzymatic Synthesis of Glycosides and Glucuronides.

7.1 Glycosynthase-assisted Oligosaccharide Synthesis (AdrianScaffidi and Robert V. Stick).

7.2 Glycosyl Azides: Novel Substrates for EnzymaticTransglycosylations (ladimír Krˇen and PavlaBojarová).

7.3 Facile Synthesis of Alkyl -D-Glucopyranosides from D-Glucoseand the Corresponding Alcohols Using Fruit Seed Meals (Wen-Ya Lu,Guo-Qiang Lin, Hui-Lei Yu, Ai-Ming Tong and Jian-He Xu).

7.4 Laccase-mediated Oxidation of Natural Glycosides (CosimoChiriví, Francesca Sagui and Sergio Riva).

7.5 Biocatalysed Synthesis of Monoglucuronides ofHydroxytyrosol, Tyrosol, Homovanillic Alcohol and3-(40-Hydroxyphenyl)propanol Using Liver Cell Microsomal Fractions(Olha Khymenets, Pere Clapés, Teodor Parella,María-Isabel Covas, Rafael de la Torre, and JesusJoglar).

7.6 Synthesis of the Acyl Glucuronide of Mycophenolic Acid(Matthias Kittelmann, Lukas Oberer, Reiner Aichholz and OresteGhisalba).

8 Synthesis of Cyanohydrins Using Hydroxynitrile Lyases.

8.1 Synthesis of (S)-2-Hydroxy-2-methylbutyric Acid by aChemoenzymatic Methodology (Manuela Avi and Herfried Griengl).

8.2 (S)-Selective Cyanohydrin Formation from Aromatic KetonesUsing Hydroxynitrile Lyases (Chris Roberge, Fred Fleitz and PaulDevine).

8.3 Hydroxynitrile-lyase-catalysed Synthesis of Enantiopure(S)-Acetophenone Cyanohydrins (Jan von Langermann, Annett Mell,Eckhard Paetzold and Udo Kragl).

8.4 (R)- and (S)-Cyanohydrin Formation fromPyridine-3-carboxaldehydeUsingCLEATM-immobilizedHydroxynitrileLyases (Chris Roberge, Fred Fleitz and Paul Devine).

8.5 A New (R)-Hydroxynitrile Lyase from Prunus mume forAsymmetric Synthesis of Cyanohydrins (Yasuhisa Asano).

9 Synthesis of Chiral sec-Alcohols by Ketone Reduction.

9.1 Asymmetric Synthesis of(S)-Bis(trifluoromethyl)phenylethanol by Biocatalytic Reduction ofBis(trifluoromethyl)acetophenone (David Pollard, Matthew Truppo andJeffrey Moore).

9.2 Enantioselective and Diastereoselective Enzyme-catalyzedDynamic Kinetic Resolution of an Unsaturated Ketone (Birgit Kosjek,David Tellers and Jeffrey Moore).

9.3 Enzyme-catalysed Synthesis of -Alkyl—hydroxy Ketones andEsters by Isolated Ketoreductases (Ioulia Smonou and DimitrisKalaitzakis).

9.4 Asymmetric Reduction of Phenyl Ring-containing Ketones UsingXerogel-encapsulated W110A Secondary Alcohol Dehydrogenase fromThermoanaerobacter ethanolicus (Musa M. Musa, Karla I.Ziegelmann-Fjeld, Claire Vieille, J. Gregory Zeikus and Robert S.Phillips).

9.5 (R)- and (S)-Enantioselective Diaryl Methanol SynthesisUsing Enzymatic Reduction of Diaryl Ketones (Matthew Truppo, KristaMorley, David Pollard and Paul Devine).

9.6 Highly Enantioselective and Efficient Synthesis of Methyl(R)-o-Chloromandelate, Key Intermediate for Clopidogrel Synthesis,with Recombinant Escherichia coli (Tadashi Ema, Nobuyasu Okita,Sayaka Ide and Takashi Sakai).

10 Reduction of Functional Groups.

10.1 Reduction of Carboxylic Acids by Carboxylic Acid ReductaseHeterologously Expressed in Escherichia coli (Andrew S. Lamm,Arshdeep Khare and John P.N. Rosazza).

10.2 Light-driven Stereoselective Biocatalytic Oxidations andReductions (Andreas Taglieber, Frank Schulz, Frank Hollmann, MonikaRusek and Manfred T. Reetz).

10.3 Unnatural Amino Acids by Enzymatic Transamination:Synthesis of Glutamic Acid Analogues with AspartateAminotransferase (Thierry Gefflaut, Emmanuelle Sagot and JeanBolte).

10.4 Synthesis of L-Pipecolic Acid with1-Piperidine-2-carboxylate Reductase from Pseudomonas putida(Hisaaki Mihara and Nobuyoshi Esaki).

10.5 Synthesis of Substituted Derivatives of L-Phenylalanine andof other Non-natural L-Amino Acids Using Engineered Mutants ofPhenylalanine Dehydrogenase (Philip Conway, Francesca Paradisi andPaul Engel).

11 Enzymatic Oxidation Chemistry.

11.1 Monoamine Oxidase-catalysed Reactions: Application Towardsthe Chemo-enzymatic Deracemization of the Alkaloid(–)-Crispine A (Andrew J. Ellis, Renate Reiss, Timothy J.Snape and Nicholas J. Turner

11.2 Glucose Oxidase-catalysed Synthesis of). Aldonic Acids(Fabio Pezzotti, Helene Therisod and Michel Therisod).

11.3 Oxidation and Halo-hydroxylation of Monoterpenes withChloroperoxidase from Leptoxyphium fumago (Bjoern-Arne Kaup,Umberto Piantini, Matthias Wüst and Jens

Schrader).

11.4 Chloroperoxidase-catalyzed Oxidation of PhenylMethylsulfide in Ionic Liquids (Cinzia Chiappe).

11.5 Stereoselective Synthesis of -Hydroxy Sulfoxides Catalyzedby Cyclohexanone Monooxygenase (Stefano Colonna, Nicoletta Gaggero,Sara Pellegrino and Francesca

Zambianchi).

11.6 Enantioselective Kinetic Resolution of Racemic3-Phenylbutan-2-one Using a Baeyer–Villiger Monooxygenase(Anett Kirschner and Uwe T. Bornscheuer).

11.7 Desymmetrization of 1-Methylbicyclo[3.3.0]octane-2,8-dioneby the Retro-claisenase 6-Oxo Camphor Hydrolase (Gideon Grogan andCheryl Hill).

11.8 Synthesis of Optically Pure Chiral Lactones byCyclopentadecanone Monooxygenase-catalyzed Baeyer–VilligerOxidations (Shaozhao Wang, Jianzhong Yang and Peter C.K. Lau).

12 Whole-cell Oxidations and Dehalogenations.

12.1 Biotransformations of Naphthalene to 4-Hydroxy-1-tetraloneby Streptomyces griseus NRRL 8090 (Arshdeep Khare, Andrew S. Lammand John P.N. Rosazza).

12.2 Hydroxylation of Imidacloprid for the Synthesis of OlefinImidacloprid by Stenotrophomonas maltophilia CGMCC 1.1788 (ShengYuan and Yi-jun Dai).

12.3 Biocatalytic Synthesis of 6-Hydroxy Fluvastatin usingMotierella rammaniana DSM 62752 in Shake Flask Culture and onMulti-gram Scale using a Wave Bioreactor (Matthias Kittelmann,Maria Serrano Correia, Anton Kuhn, Serge Parel, JürgenKu¨hnol, Reiner Aichholz, Monique Ponelle and OresteGhisalba).

12.4 Synthesis of 1-Adamantanol from Adamantane throughRegioselective Hydroxylation by Streptomyces griseoplanus Cells(Koichi Mitsukura, Yoshinori Kondo, Toyokazu Yoshida and ToruNagasawa).

12.5 Enantioselective Benzylic Microbial Hydroxylation of Indanand Tetralin (Renata P. Limberger, Cleber V. Ursini, Paulo J.S.Moran and J. Augusto R. Rodrigues).

12.6 Stereospecific Biotransformation of (R,S)-Linalool byCorynespora cassiicola DSM 62475 into Linalool Oxides(Marco-Antonio Mirata and Jens Schrader).

12.7 The Biocatalytic Synthesis of 4-Fluorocatechol fromFluorobenzene (Louise C. Nolan and Kevin E. O’Connor).

12.8 Synthesis of Enantiopure (S)-Styrene Oxide by SelectiveOxidation of Styrene by Recombinant Escherichia coli JM101 (pSPZ10)(Katja Buehler and Andreas Schmid).

12.9 Biotransformation of -Bromo and ,0-Dibromo Alkanone into-Hydroxyketone and -Diketone by Spirulina platensis (TakamitsuUtsukihara and C. Akira Horiuchi).

Index.

What People are Saying About This

From the Publisher

"Chapters cover key biotransformations from the literature, detailing the procedures used, the sources of the starting materials and reagents, references, and tips and advice, where appropriate." (JACS, 2010)

"It starts with a review of the current use of biocatalysis in the pharmaceutical industry. Although this is focused on a large pharmaceutical company (GlaxoSmithKline), it covers a wide variety of aspects of the industry and offers insightful comparisons of biocatalysis with ‘traditional' organic synthesis." (Chemistry World, July 2010)

"I can recommend to all those who are interesting in carrying out biotransformations in the laboratory, and the book should help persuade those who have never used a biotransformation in an organic synthesis, to try one for the first time." (Organic Process Research & Development Journal, 2010)

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