Stereoselectivity of Four (R)-Selective Transaminases for the Asymmetric Amination of Ketones

Authors

  • Francesco G. Mutti,

    1. Institute of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria, Fax: (+43)-316-380-9840
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  • Christine S. Fuchs,

    1. Institute of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria, Fax: (+43)-316-380-9840
    2. ACIB GmbH, Department of Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria
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  • Desiree Pressnitz,

    1. Institute of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria, Fax: (+43)-316-380-9840
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  • Johann H. Sattler,

    1. Institute of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria, Fax: (+43)-316-380-9840
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  • Wolfgang Kroutil

    Corresponding author
    1. Institute of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria, Fax: (+43)-316-380-9840
    • Institute of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria, Fax: (+43)-316-380-9840
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Abstract

Four (R)-ω-transaminases originating from Hyphomonas neptunium (HN-ωTA), Aspergillus terreus (AT-ωTA) and Arthrobacter sp. (ArR-ωTA), as well as an evolved transaminase (ArRmut11-ωTA) were successfully employed for the amination of prochiral ketones leading to optically pure (R)-amines. The first three transaminases displayed perfect stereoselectivity for the amination of all substrates tested (ee >99%). Furthermore, the transaminase AT-ωTA led in most cases to better conversion than ArR-ωTA and HN-ωTA using D-alanine as amine donor. α-Tetralone, which was the only substrate not accepted by HN-ωTA, ArR-ωTA, and AT-ωTA, was successfully transformed with perfect enantioselectivity (ee >99%) into the corresponding optically pure amine employing the variant ArRmut11-ωTA.

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