Literature DB >> 20461261

Chemoenzymatic asymmetric total synthesis of (S)-Rivastigmine using omega-transaminases.

Michael Fuchs1, Dominik Koszelewski, Katharina Tauber, Wolfgang Kroutil, Kurt Faber.   

Abstract

A straightforward, high-yielding, chemoenzymatic total synthesis of enantiopure (S)-Rivastigmine was developed using various omega-transaminases for the asymmetric amination of appropriate acetophenone precursors. Optimisation of the biotransformation allowed scale-up and the total synthesis of (S)-Rivastigmine.

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Year:  2010        PMID： 20461261     DOI： 10.1039/c0cc00585a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  10 in total

1.  ω-Transaminase from Ochrobactrum anthropi is devoid of substrate and product inhibitions.

Authors:  Eul-Soo Park; Jong-Shik Shin
Journal:  Appl Environ Microbiol       Date:  2013-04-12       Impact factor: 4.792

2.  Asymmetric synthesis of nonracemic primary amines via spiroborate-catalyzed reduction of pure (E)- and (Z)-O-benzyloximes: applications toward the synthesis of calcimimetic agents.

Authors:  Wenhua Ou; Sandraliz Espinosa; Héctor J Meléndez; Silvia M Farré; Jaime L Alvarez; Valerie Torres; Ileanne Martínez; Kiara M Santiago; Margarita Ortiz-Marciales
Journal:  J Org Chem       Date:  2013-05-13       Impact factor: 4.354

3.  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

4.  The substrate specificity, enantioselectivity and structure of the (R)-selective amine : pyruvate transaminase from Nectria haematococca.

Authors:  Christopher Sayer; Ruben J Martinez-Torres; Nina Richter; Michail N Isupov; Helen C Hailes; Jennifer A Littlechild; John M Ward
Journal:  FEBS J       Date:  2014-04-07       Impact factor: 5.542

5.  The Industrial Age of Biocatalytic Transamination.

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

6.  Improvement of whole-cell transamination with Saccharomyces cerevisiae using metabolic engineering and cell pre-adaptation.

Authors:  Nora Weber; Marie Gorwa-Grauslund; Magnus Carlquist
Journal:  Microb Cell Fact       Date:  2017-01-03       Impact factor: 5.328

Review 7.  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

8.  Structural studies of Pseudomonas and Chromobacterium ω-aminotransferases provide insights into their differing substrate specificity.

Authors:  Christopher Sayer; Michail N Isupov; Aaron Westlake; Jennifer A Littlechild
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2013-03-14

9.  Direct Asymmetric Reductive Amination for the Synthesis of (S)-Rivastigmine.

Authors:  Guorui Gao; Shaozhi Du; Yang Yang; Xue Lei; Haizhou Huang; Mingxin Chang
Journal:  Molecules       Date:  2018-08-31       Impact factor: 4.411

10.  Concise Chemoenzymatic Three Step Total Synthesis of Isosolenopsin Through Medium Engineering.

Authors:  Robert C Simon; Christine S Fuchs; Horst Lechner; Ferdinand Zepeck; Wolfgang Kroutil
Journal:  European J Org Chem       Date:  2013-06-01
  10 in total

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