Nitrile as Activating Group in the Asymmetric Bioreduction of β-Cyanoacrylic Acids Catalyzed by Ene-Reductases

Asymmetric bioreduction of an (E)‐β‐cyano‐2,4‐dienoic acid derivative by ene‐reductases allowed a shortened access to a precursor of pregabalin [(S)‐3‐(aminomethyl)‐5‐methylhexanoic acid] possessing the desired configuration in up to 94% conversion and >99% ee. Deuterium labelling studies showed...

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Published inAdvanced synthesis & catalysis Vol. 356; no. 8; pp. 1878 - 1882
Main Authors Winkler, Christoph K., Clay, Dorina, Turrini, Nikolaus G., Lechner, Horst, Kroutil, Wolfgang, Davies, Simon, Debarge, Sebastien, O'Neill, Pat, Steflik, Jeremy, Karmilowicz, Mike, Wong, John W., Faber, Kurt
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 26.05.2014
WILEY‐VCH Verlag
Subjects
biocatalysis
cyanoacrylates
CC reduction
ene-reductases
pregabalin
Updates
pregabalin
cyanoacrylates
C=C reduction
ene-reductases
biocatalysis
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Abstract Asymmetric bioreduction of an (E)‐β‐cyano‐2,4‐dienoic acid derivative by ene‐reductases allowed a shortened access to a precursor of pregabalin [(S)‐3‐(aminomethyl)‐5‐methylhexanoic acid] possessing the desired configuration in up to 94% conversion and >99% ee. Deuterium labelling studies showed that the nitrile moiety was the preferred activating/anchor group in the active site of the enzyme over the carboxylic acid or the corresponding methyl ester.
AbstractList Asymmetric bioreduction of an (E)-β-cyano-2,4-dienoic acid derivative by ene-reductases allowed a shortened access to a precursor of pregabalin [(S)-3-(aminomethyl)-5-methylhexanoic acid] possessing the desired configuration in up to 94% conversion and >99% ee. Deuterium labelling studies showed that the nitrile moiety was the preferred activating/anchor group in the active site of the enzyme over the carboxylic acid or the corresponding methyl ester.
Abstract Asymmetric bioreduction of an ( E )‐β‐cyano‐2,4‐dienoic acid derivative by ene‐reductases allowed a shortened access to a precursor of pregabalin [( S )‐3‐(aminomethyl)‐5‐methylhexanoic acid] possessing the desired configuration in up to 94% conversion and >99% ee . Deuterium labelling studies showed that the nitrile moiety was the preferred activating/anchor group in the active site of the enzyme over the carboxylic acid or the corresponding methyl ester. magnified image
Asymmetric bioreduction of an ( E )-β-cyano-2,4-dienoic acid derivative by ene-reductases allowed a shortened access to a precursor of pregabalin [( S )-3-(aminomethyl)-5-methylhexanoic acid] possessing the desired configuration in up to 94% conversion and >99% ee . Deuterium labelling studies showed that the nitrile moiety was the preferred activating/anchor group in the active site of the enzyme over the carboxylic acid or the corresponding methyl ester.
Asymmetric bioreduction of an ( )-β-cyano-2,4-dienoic acid derivative by ene-reductases allowed a shortened access to a precursor of pregabalin [( )-3-(aminomethyl)-5-methylhexanoic acid] possessing the desired configuration in up to 94% conversion and >99% . Deuterium labelling studies showed that the nitrile moiety was the preferred activating/anchor group in the active site of the enzyme over the carboxylic acid or the corresponding methyl ester.
Author Kroutil, Wolfgang
Winkler, Christoph K.
Clay, Dorina
Turrini, Nikolaus G.
O'Neill, Pat
Lechner, Horst
Davies, Simon
Karmilowicz, Mike
Debarge, Sebastien
Wong, John W.
Faber, Kurt
Steflik, Jeremy
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  organization: Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria, Fax: (+43)-316-380-9840; phone: (+43)-316-380-5332
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  givenname: Dorina
  surname: Clay
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  organization: Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria, Fax: (+43)-316-380-9840; phone: (+43)-316-380-5332
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  givenname: Nikolaus G.
  surname: Turrini
  fullname: Turrini, Nikolaus G.
  organization: Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria, Fax: (+43)-316-380-9840; phone: (+43)-316-380-5332
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  givenname: Horst
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  givenname: Wolfgang
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– sequence: 6
  givenname: Simon
  surname: Davies
  fullname: Davies, Simon
  organization: Pfizer Global Supply, Process Development Centre, Loughbeg, County Cork, Ireland
– sequence: 7
  givenname: Sebastien
  surname: Debarge
  fullname: Debarge, Sebastien
  organization: Pfizer Global Supply, Process Development Centre, Loughbeg, County Cork, Ireland
– sequence: 8
  givenname: Pat
  surname: O'Neill
  fullname: O'Neill, Pat
  organization: Pfizer Global Supply, Process Development Centre, Loughbeg, County Cork, Ireland
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  givenname: Jeremy
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  organization: Pfizer Worldwide R&D, Chemical R&D, Eastern Point Rd, Groton, CT 06340, USA
– sequence: 10
  givenname: Mike
  surname: Karmilowicz
  fullname: Karmilowicz, Mike
  organization: Pfizer Worldwide R&D, Chemical R&D, Eastern Point Rd, Groton, CT 06340, USA
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  givenname: John W.
  surname: Wong
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  email: john.w.wong@pfizer.com
  organization: Pfizer Worldwide R&D, Chemical R&D, Eastern Point Rd, Groton, CT 06340, USA
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  givenname: Kurt
  surname: Faber
  fullname: Faber, Kurt
  email: kurt.faber@uni-graz.at
  organization: Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria, Fax: (+43)-316-380-9840; phone: (+43)-316-380-5332
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Copyright 2014 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. 2014
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Issue 8
Keywords pregabalin
cyanoacrylates
C=C reduction
ene-reductases
biocatalysis
Language English
License 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
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Snippet Asymmetric bioreduction of an (E)‐β‐cyano‐2,4‐dienoic acid derivative by ene‐reductases allowed a shortened access to a precursor of pregabalin...
Asymmetric bioreduction of an ( )-β-cyano-2,4-dienoic acid derivative by ene-reductases allowed a shortened access to a precursor of pregabalin [(...
Abstract Asymmetric bioreduction of an ( E )‐β‐cyano‐2,4‐dienoic acid derivative by ene‐reductases allowed a shortened access to a precursor of pregabalin [( S...
Asymmetric bioreduction of an (E)-β-cyano-2,4-dienoic acid derivative by ene-reductases allowed a shortened access to a precursor of pregabalin...
Asymmetric bioreduction of an ( E )-β-cyano-2,4-dienoic acid derivative by ene-reductases allowed a shortened access to a precursor of pregabalin [( S...
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SubjectTerms biocatalysis
cyanoacrylates
CC reduction
ene-reductases
pregabalin
Updates
Title Nitrile as Activating Group in the Asymmetric Bioreduction of β-Cyanoacrylic Acids Catalyzed by Ene-Reductases
URI https://api.istex.fr/ark:/67375/WNG-FLLP0495-G/fulltext.pdf
https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fadsc.201301055
https://www.ncbi.nlm.nih.gov/pubmed/26190962
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https://pubmed.ncbi.nlm.nih.gov/PMC4498475
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