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Formal Asymmetric Biocatalytic Reductive Amination

Authors

  • Dominik Koszelewski Dr.,

    1. Research Centre Applied Biocatalysis, c/o Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria), Fax: (+43) 316-380-9840
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  • Iván Lavandera Dr.,

    1. Research Centre Applied Biocatalysis, c/o Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria), Fax: (+43) 316-380-9840
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  • Dorina Clay,

    1. Research Centre Applied Biocatalysis, c/o Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria), Fax: (+43) 316-380-9840
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  • Georg M. Guebitz Prof.,

    1. Institute of Environmental Biotechnology, Research Centre Applied Biocatalysis, University of Technology, Petersgasse 12, 8010 Graz (Austria)
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  • David Rozzell Dr.,

    1. Codexis, Inc., Redwood City, CA (USA)
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  • Wolfgang Kroutil Prof.

    1. Research Centre Applied Biocatalysis, c/o Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria), Fax: (+43) 316-380-9840
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  • Financial support by the FFG and the Province of Styria is gratefully acknowledged. Codexis is thanked for providing various enzymes.

Abstract

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All for one: A combination of three biocatalysts (ω-transaminase, alanine dehydrogenase, and an enzyme such as formate dehydrogenase for cofactor recycling) catalyze a cascade to achieve the asymmetric transformation of a ketone into a primary α-chiral unprotected amine through a formal stereoselective reductive amination (see scheme). Only ammonia and the reducing agent (formate) are consumed during this reaction.

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