Artificial Multi-Enzyme Networks for the Asymmetric Amination of sec-Alcohols

Authors

  • Katharina Tauber,

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

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

    1. Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria), Fax: (+43) 316-380-9840
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  • Julia Pitzer,

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

    1. Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria), Fax: (+43) 316-380-9840
    2. ACIB GmbH, c/o Heinrichstrasse 28, 8010 Graz (Austria)
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  • Dr. Dominik Koszelewski,

    1. Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria), Fax: (+43) 316-380-9840
    2. ACIB GmbH, c/o Heinrichstrasse 28, 8010 Graz (Austria)
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  • Prof. Kurt Faber,

    1. Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria), Fax: (+43) 316-380-9840
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  • Jan Pfeffer,

    1. Evonik Industries AG, CREAVIS Technologies & Innovation, Paul-Baumann-Strasse 1, 45772 Marl (Germany)
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  • Thomas Haas,

    1. Evonik Industries AG, CREAVIS Technologies & Innovation, Paul-Baumann-Strasse 1, 45772 Marl (Germany)
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  • Prof. Wolfgang Kroutil

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

Various artificial network designs that involve biocatalysts were tested for the asymmetric amination of sec-alcohols to the corresponding α-chiral primary amines. The artificial systems tested involved three to five redox enzymes and were exemplary of a range of different sec-alcohol substrates. Alcohols were oxidised to the corresponding ketone by an alcohol dehydrogenase. The ketones were subsequently aminated by employing a ω-transaminase. Of special interest were redox-neutral designs in which the hydride abstracted in the oxidation step was reused in the amination step of the cascade. Under optimised conditions up to 91 % conversion of an alcohol to the amine was achieved.

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