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Catalytic Promiscuity of Halohydrin Dehalogenase and its Application in Enantioselective Epoxide Ring Opening

Authors

  • Ghannia Hasnaoui-Dijoux,

    1. Groningen Biomolecular Science and Biotechnology Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands, Fax: (+31) 50-363-4165
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  • Maja Majerić Elenkov Dr.,

    1. Groningen Biomolecular Science and Biotechnology Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands, Fax: (+31) 50-363-4165
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  • Jeffrey H. Lutje Spelberg Dr.,

    1. Groningen Biomolecular Science and Biotechnology Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands, Fax: (+31) 50-363-4165
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  • Bernhard Hauer Prof. Dr.,

    1. BASF AG, Fine Chemicals and Biocatalysis Research, 67056 Ludwigshafen, Germany
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  • Dick B. Janssen Prof. Dr.

    1. Groningen Biomolecular Science and Biotechnology Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands, Fax: (+31) 50-363-4165
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Abstract

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Easy virtue: Halohydrin dehalogenase is a highly promiscuous enzyme that can catalyze enantioselective epoxide ring opening with at least nine different anionic nucleophiles (see scheme). Its capacity to form carbon–nitrogen, carbon–oxygen, carbon–sulfur, and carbon–carbon bonds makes it possible to use this enzyme for the preparation of a range of highly enantioenriched β-substituted alcohols or derivatives thereof, including cyanoalcohols, nitroalcohols, and oxazolidinones.

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