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Regio- and Stereoselective Oxidative Phenol Coupling in Aspergillus niger

Authors

  • Dr. Christian Gil Girol,

    1. Institut für Pharmazeutische Wissenschaften, Albert-Ludwigs-Universität Freiburg, Albertstraße 25, 79104 Freiburg (Germany)
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  • Dr. Katja M. Fisch,

    1. School of Chemistry, University of Bristol, Bristol BS81TS (UK)
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  • Dr. Thorsten Heinekamp,

    1. Department of Molecular and Applied Microbiology, Leibniz-Institute for Natural Product Research and Infection Biology, 07745 Jena (Germany)
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  • Jun.-Prof. Dr. Stefan Günther,

    1. Institut für Pharmazeutische Wissenschaften, Albert-Ludwigs-Universität Freiburg, Albertstraße 25, 79104 Freiburg (Germany)
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  • Dr. Wolfgang Hüttel,

    1. Institut für Pharmazeutische Wissenschaften, Albert-Ludwigs-Universität Freiburg, Albertstraße 25, 79104 Freiburg (Germany)
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  • Prof. Dr. Jörn Piel,

    1. Kekulé Institut für Organische Chemie und Biochemie, Universität Bonn, 53121 Bonn (Germany)
    2. Present address: Institute of Microbiology, ETH Zürich, Wolfgang-Pauli-Str. 10, 8093 Zürich (Switzerland)
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  • Prof. Dr. Axel A. Brakhage,

    1. Department of Molecular and Applied Microbiology, Leibniz-Institute for Natural Product Research and Infection Biology, 07745 Jena (Germany)
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  • Prof. Dr. Michael Müller

    Corresponding author
    1. Institut für Pharmazeutische Wissenschaften, Albert-Ludwigs-Universität Freiburg, Albertstraße 25, 79104 Freiburg (Germany)
    • Institut für Pharmazeutische Wissenschaften, Albert-Ludwigs-Universität Freiburg, Albertstraße 25, 79104 Freiburg (Germany)
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  • Financial support of this work by the DFG within the scope of SPP1152 is gratefully acknowledged. We thank V. Brecht for technical assistance and Prof. Dr. Ing. V. Meyer, Institut für Biotechnologie, TU Berlin (Germany) for the plasmid pMA171.

Abstract

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Piecing it together: Aspergillus niger produces kotanin (see structure) by dimerization of the monomeric, polyketide-synthase-derived (PKS) 7-demethylsiderin. A combined approach, comprising bioinformatics and gene-deletion experiments, identified the biosynthetic cluster responsible for kotanin production. Homology modeling and substrate docking provide a rationale for the regio- and stereoselective phenol coupling reaction.

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