Literature DB >> 19785441

Deracemization of mexiletine biocatalyzed by omega-transaminases.

Dominik Koszelewski1, Desiree Pressnitz, Dorina Clay, Wolfgang Kroutil.   

Abstract

(S)- as well as (R)-mexiletine [1-(2,6-dimethylphenoxy)-2-propanamine], a chiral orally effective antiarrhythmic agent, was prepared by deracemization starting from the commercially available racemic amine using omega-transaminases in up to >99% ee and conversion with 97% isolated yield by a one-pot two-step procedure. The absolute configuration could be easily switched to the other enantiomer, just by switching the order of the applied transaminases. The cosubstrate pyruvate needed in the first oxidative step was recycled by using an amino acid oxidase.

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Year:  2009        PMID: 19785441     DOI: 10.1021/ol901834x

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  9 in total

1.  Asymmetric Preparation of prim-, sec-, and tert-Amines Employing Selected Biocatalysts.

Authors:  Wolfgang Kroutil; Eva-Maria Fischereder; Christine S Fuchs; Horst Lechner; Francesco G Mutti; Desiree Pressnitz; Aashrita Rajagopalan; Johann H Sattler; Robert C Simon; Elina Siirola
Journal:  Org Process Res Dev       Date:  2013-04-22       Impact factor: 3.317

Review 2.  Recent biocatalytic oxidation-reduction cascades.

Authors:  Joerg H Schrittwieser; Johann Sattler; Verena Resch; Francesco G Mutti; Wolfgang Kroutil
Journal:  Curr Opin Chem Biol       Date:  2010-12-02       Impact factor: 8.822

3.  The Industrial Age of Biocatalytic Transamination.

Authors:  Michael Fuchs; Judith E Farnberger; Wolfgang Kroutil
Journal:  European J Org Chem       Date:  2015-09-23

Review 4.  Transaminases for industrial biocatalysis: novel enzyme discovery.

Authors:  Stephen A Kelly; Stefan Mix; Thomas S Moody; Brendan F Gilmore
Journal:  Appl Microbiol Biotechnol       Date:  2020-04-16       Impact factor: 4.813

5.  Highly efficient production of chiral amines in batch and continuous flow by immobilized ω-transaminases on controlled porosity glass metal-ion affinity carrier.

Authors:  Wesley Böhmer; Tanja Knaus; Alexey Volkov; Thierry K Slot; N Raveendran Shiju; Karim Engelmark Cassimjee; Francesco G Mutti
Journal:  J Biotechnol       Date:  2018-12-11       Impact factor: 3.307

6.  Recombinant l-Amino Acid Oxidase with Broad Substrate Spectrum for Co-substrate Recycling in (S)-Selective Transaminase-Catalyzed Kinetic Resolutions.

Authors:  Tobias Heinks; Jannik Paulus; Simon Koopmeiners; Tobias Beuel; Norbert Sewald; Matthias Höhne; Uwe T Bornscheuer; Gabriele Fischer von Mollard
Journal:  Chembiochem       Date:  2022-07-05       Impact factor: 3.461

7.  Crystal structure of an (R)-selective ω-transaminase from Aspergillus terreus.

Authors:  Andrzej Łyskowski; Christian Gruber; Georg Steinkellner; Martin Schürmann; Helmut Schwab; Karl Gruber; Kerstin Steiner
Journal:  PLoS One       Date:  2014-01-30       Impact factor: 3.240

8.  Expansion of the Substrate Specificity of Porcine Kidney D-Amino Acid Oxidase for S-Stereoselective Oxidation of 4-Cl-Benzhydrylamine.

Authors:  Kazuyuki Yasukawa; Fumihiro Motojima; Atsushi Ono; Yasuhisa Asano
Journal:  ChemCatChem       Date:  2018-07-13       Impact factor: 5.686

9.  Genome mining and characterisation of a novel transaminase with remote stereoselectivity.

Authors:  D P Gavin; F J Reen; J Rocha-Martin; I Abreu-Castilla; D F Woods; A M Foley; P A Sánchez-Murcia; M Schwarz; P O'Neill; A R Maguire; F O'Gara
Journal:  Sci Rep       Date:  2019-12-30       Impact factor: 4.379

  9 in total

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