Biocatalytic Enantioselective Oxidative C[BOND]C Coupling by Aerobic C[BOND]H Activation

Authors

  • Joerg H. Schrittwieser,

    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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    • These authors contributed equally to this work.

  • Verena Resch,

    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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    • These authors contributed equally to this work.

  • 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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  • Wolf-Dieter Lienhart,

    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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  • Katharina Durchschein,

    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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  • Dr. Andreas Winkler,

    1. Institute of Biochemistry, Graz University of Technology, Petersgasse 12, 8010 Graz (Austria)
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  • Prof. Dr. Karl Gruber,

    1. Institute of Molecular Biosciences, University of Graz, Humboldtstraße 50/III, 8010 Graz (Austria)
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  • Prof. Dr. Peter Macheroux,

    1. Institute of Biochemistry, Graz University of Technology, Petersgasse 12, 8010 Graz (Austria)
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  • Prof. Dr. 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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  • This study was financed by the Austrian Science Fund (FWF Project P20903-N17 and P22115-N17). We thank the European Commission (MC-ITN Biotrains, grant agreement no.: 238531) for financial support. We thank Christoph Göbl for measuring CD spectra and Bernd Werner for NMR measurements.

Abstract

original image

Bridging the gap: The berberine bridge enzyme (BBE) was employed for the first preparative oxidative biocatalytic C[BOND]C coupling that leads to a new intramolecular bond. This unique transformation requires O2 as sole stoichiometric oxidant and gives access to novel optically pure (S)-berbine 2 and (R)-1-benzyl-1,2,3,4-tetrahydroisoquinoline 1 alkaloid derivatives by kinetic resolution.

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