Synthesis of Aliphatic and α-Halogenated Ketone Cyanohydrins with the Hydroxynitrile Lyase from Manihot esculenta

Authors

  • Johannes Diebler,

    1. University of Rostock, Department of Chemistry, Industrial Chemistry, Albert-Einstein-Strasse 3 A, 18059 Rostock (Germany), Fax: (+49) 381-498-6452
    2. Leibniz Institute for Catalysis (LIKAT) Rostock, Organocatalysis, Albert-Einstein-Strasse 29 a, 18059 Rostock (Germany)
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  • Dr. Jan von Langermann,

    1. University of Rostock, Department of Chemistry, Industrial Chemistry, Albert-Einstein-Strasse 3 A, 18059 Rostock (Germany), Fax: (+49) 381-498-6452
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  • Annett Mell,

    1. University of Rostock, Department of Chemistry, Industrial Chemistry, Albert-Einstein-Strasse 3 A, 18059 Rostock (Germany), Fax: (+49) 381-498-6452
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  • Dr. Martin Hein,

    1. University of Rostock, Department of Chemistry, Organic Chemistry, Albert-Einstein-Strasse 3 A, 18059 Rostock (Germany)
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  • Prof. Dr. Peter Langer,

    1. University of Rostock, Department of Chemistry, Organic Chemistry, Albert-Einstein-Strasse 3 A, 18059 Rostock (Germany)
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  • Prof. Dr. Udo Kragl

    Corresponding author
    1. University of Rostock, Department of Chemistry, Industrial Chemistry, Albert-Einstein-Strasse 3 A, 18059 Rostock (Germany), Fax: (+49) 381-498-6452
    • University of Rostock, Department of Chemistry, Industrial Chemistry, Albert-Einstein-Strasse 3 A, 18059 Rostock (Germany), Fax: (+49) 381-498-6452

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Abstract

The potential of the hydroxynitrile lyase from Manihot esculenta towards ketone substrates was investigated. It was observed that the length of the aliphatic chain is a key parameter for the conversion of aliphatic, non-branched ketones. Smaller substrates are readily converted with high enantioselectivites, but the elongation of the chain length causes a significant loss in enzyme activity. For a number of halogenated, herein especially fluorinated, acetophenone derivatives the corresponding cyanohydrins have been synthesized with good to moderate enantioselectivities.

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