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

doi:10.1002/anie.201510554

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	3144-3147
Number of pages	4
Journal	Angewandte Chemie International Edition
Volume	55
Issue number	9
Early online date	2 Feb 2016
DOIs	https://doi.org/10.1002/anie.201510554
Publication status	Published - 24 Feb 2016

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© Wiley 2016. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details

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© Wiley 2016. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details
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Gideon James Grogan
- gideon.groganyork.acuk
- Chemistry - Professor
Person: Academic

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

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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Cuetos, A, García-Ramos, M, Fischereder, E-M, Díaz-Rodríguez, A, Grogan, G, Gotor, V, Kroutil, W & Lavandera, I 2016, 'Catalytic Promiscuity of Transaminases: Preparation of Enantioenriched β-Fluoroamines by Formal Tandem Hydrodefluorination/Deamination', Angewandte Chemie International Edition, vol. 55, no. 9, pp. 3144-3147. https://doi.org/10.1002/anie.201510554

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AU - Cuetos, Aníbal

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AU - Fischereder, Eva-Maria

AU - Díaz-Rodríguez, Alba

AU - Grogan, Gideon

AU - Gotor, Vicente

AU - Kroutil, Wolfgang

AU - Lavandera, Iván

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N2 - 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.

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

Abstract

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Gideon James Grogan

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