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

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

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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.

Original languageEnglish
Pages (from-to)3144-3147
Number of pages4
JournalAngewandte Chemie International Edition
Issue number9
Early online date2 Feb 2016
Publication statusPublished - 24 Feb 2016

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