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Biocatalytic Friedel–Crafts Alkylation Using Non-natural Cofactors

Authors

  • Harald Stecher Dipl.-Ing.,

    1. Kompetenzzentrum Angewandte Biokatalyse, Petersgasse 14, 8010 Graz (Austria), Fax: (+43) 316-873-8740
    2. Institut für Organische Chemie, Technische Universität Graz, Stremayrgasse 16, 8010 Graz (Austria)
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  • Martin Tengg M. Sc.,

    1. Kompetenzzentrum Angewandte Biokatalyse, Petersgasse 14, 8010 Graz (Austria), Fax: (+43) 316-873-8740
    2. Institut für Molekulare Biotechnologie, Technische Universität Graz (Austria)
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  • Bernhard J. Ueberbacher Dr.,

    1. Kompetenzzentrum Angewandte Biokatalyse, Petersgasse 14, 8010 Graz (Austria), Fax: (+43) 316-873-8740
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  • Peter Remler Dr.,

    1. Kompetenzzentrum Angewandte Biokatalyse, Petersgasse 14, 8010 Graz (Austria), Fax: (+43) 316-873-8740
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  • Helmut Schwab Prof. Dr.,

    1. Institut für Molekulare Biotechnologie, Technische Universität Graz (Austria)
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  • Herfried Griengl Prof. Dr.,

    1. Kompetenzzentrum Angewandte Biokatalyse, Petersgasse 14, 8010 Graz (Austria), Fax: (+43) 316-873-8740
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  • Mandana Gruber-Khadjawi Dr.

    1. Kompetenzzentrum Angewandte Biokatalyse, Petersgasse 14, 8010 Graz (Austria), Fax: (+43) 316-873-8740
    2. Institut für Organische Chemie, Technische Universität Graz, Stremayrgasse 16, 8010 Graz (Austria)
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  • The Österreichische Forschungsförderungsgesellschaft (FFG), the Province of Styria, and the Styrian Business Promotion Agency (SFG)—within the framework of the Kplus programme as well as GASS programme within NAWI Graz—are acknowledged for financial support, as well as Birgit Krenn for technical support. M.G.-K. thanks Prof. Dr. Rolf Breinbauer for his fruitful contribution to this manuscript.

Abstract

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A novel biocatalytic protocol for C[BOND]C bond formation is described and is an equivalent to Friedel–Crafts alkylation. S-Adenosyl-L-methionine (SAM), the major methyl donor for biological methylation catalyzed by methyltransferases (Mtases), can perform alkylations (see scheme). These enzymes can accept non-natural cofactors and transfer functionalities other than methyl onto aromatic substrates.

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