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Catalytic Promiscuity of Transaminases: Preparation of Enantioenriched β-Fluoroamines by Formal Tandem Hydrodefluorination/Deamination

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Author(s)

  • Aníbal Cuetos
  • Marina García-Ramos
  • Eva-Maria Fischereder
  • Alba Díaz-Rodríguez
  • Gideon Grogan
  • Vicente Gotor
  • Wolfgang Kroutil
  • Iván Lavandera

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Publication details

JournalAngewandte Chemie International Edition
DateE-pub ahead of print - 2 Feb 2016
DatePublished (current) - 24 Feb 2016
Issue number9
Volume55
Number of pages4
Pages (from-to)3144-3147
Early online date2/02/16
Original languageEnglish

Abstract

Transaminases are valuable enzymes for industrial biocatalysis and enable the preparation of optically pure amines. For these transformations they require either an amine donor (amination of ketones) or an amine acceptor (deamination of racemic amines). Herein transaminases are shown to react with aromatic β-fluoroamines, thus leading to simultaneous enantioselective dehalogenation and deamination to form the corresponding acetophenone derivatives in the absence of an amine acceptor. A series of racemic β-fluoroamines was resolved in a kinetic resolution by tandem hydrodefluorination/deamination, thus giving the corresponding amines with up to greater than 99 % ee. This protocol is the first example of exploiting the catalytic promiscuity of transaminases as a tool for novel transformations.

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