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Catalytic Promiscuity of Transaminases: Preparation of Enantioenriched β‐Fluoroamines by Formal Tandem Hydrodefluorination/Deamination |
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| Authors: | Dr Aníbal Cuetos Marina García‐Ramos Eva‐Maria Fischereder Dr Alba Díaz‐Rodríguez Prof Gideon Grogan Prof Vicente Gotor Prof Wolfgang Kroutil Dr Iván Lavandera |
| Institution: | 1. York Structural Biology Laboratory, Department of Chemistry, University of York, Heslington, York, UK;2. Departamento de Química Orgánica e Inorgánica, University of Oviedo, Instituto Universitario de Biotecnología de Asturias, Oviedo, Spain;3. Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Graz, Austria;4. Medicines Research Centre, GlaxoSmithKline R&D Ltd, Stevenage, Hertfordshire, UK |
| 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. |
| Keywords: | amines biocatalysis enzymes fluorine kinetic resolution |