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Asymmetric Enzymatic Hydration of Hydroxystyrene Derivatives

Authors

  • Christiane Wuensch,

    1. ACIB GmbH c/o Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)
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  • Johannes Gross,

    1. ACIB GmbH c/o Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)
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  • Dr. Georg Steinkellner,

    1. ACIB GmbH c/o Institute of Molecular Biosciences, University of Graz, Humboldtstrasse 50, 8010 Graz (Austria)
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  • Prof. Karl Gruber,

    1. Institute of Molecular Biosciences, University of Graz, Humboldtstrasse 50, 8010 Graz (Austria)
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  • Dr. Silvia M. Glueck,

    Corresponding author
    1. ACIB GmbH c/o Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)
    • Silvia M. Glueck, ACIB GmbH c/o Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)===

      Kurt Faber, Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)===

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  • Prof. Kurt Faber

    Corresponding author
    1. Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)
    • Silvia M. Glueck, ACIB GmbH c/o Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)===

      Kurt Faber, Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)===

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  • This work has been supported by the Austrian BMWFJ, BMVIT, SFG, Standortagentur Tirol, and ZIT through the Austrian FFG-COMET- Funding Program. Byung-Gee Kim (School of Chemical and Biological Engineering, Seoul National University, Seoul, South Korea) is cordially thanked for the generous donation of phenolic acid decarboxylase plasmids.

Abstract

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More than one activity: Owing to their hydratase activity, phenolic acid decarboxylases catalyze the regio- and stereoselective addition of H2O across the C[DOUBLE BOND]C double bond of hydroxystyrene derivatives yielding (S)-4-(1-hydroxyethyl)phenols with up to 82 % conversion and 71 % ee. Based on structure analysis and molecular docking simulations, a catalytic mechanism for this novel enzymatic reaction is proposed.

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