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Enzymatic Racemization of Amines Catalyzed by Enantiocomplementary ω-Transaminases

Authors

  • Dr. Dominik Koszelewski,

    1. Austrian Centre of Industrial Biotechnology (ACIB) c/o, Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)
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  • Barbara Grischek,

    1. Austrian Centre of Industrial Biotechnology (ACIB) c/o, Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)
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  • Dr. Silvia M. Glueck,

    1. Austrian Centre of Industrial Biotechnology (ACIB) c/o, Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)
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  • Prof. Wolfgang Kroutil,

    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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  • Prof. Kurt Faber

    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

A strategy for the biocatalytic racemization of primary α-chiral amines was developed by employing a pair of stereocomplementary PLP-dependent ω-transaminases. The interconversion of amine enantiomers proceeded through reversible transamination by a prochiral ketone intermediate, either catalyzed by a pair of stereocomplementary ω-transaminases or by a single enzyme possessing low stereoselectivity. To tune the system, the type and concentration of a nonchiral amino acceptor proved to be crucial. Finally, racemization could be achieved by the cross-transamination of two different amines without a requirement for an external amino acceptor. Several synthetically and industrially important amines could be enzymatically racemized under mild reaction conditions.

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