Analysis of Enantiofacial Selective Epoxidation Catalyzed by Flavin-containing Monooxygenase Lsd18 Involved in Ionophore Polyether Lasalocid Biosynthesis

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  • Gaku Suzuki
    Division of Chemistry, Graduate School of Science, Hokkaido University
  • Atsushi Minami
    Division of Chemistry, Graduate School of Science, Hokkaido University
  • Mayu Shimaya
    Division of Chemistry, Graduate School of Science, Hokkaido University
  • Takeshi Kodama
    Department of Chemistry, Graduate School of Science, Osaka City University
  • Yoshiki Morimoto
    Department of Chemistry, Graduate School of Science, Osaka City University
  • Hiroki Oguri
    Division of Chemistry, Graduate School of Science, Hokkaido University
  • Hideaki Oikawa
    Division of Chemistry, Graduate School of Science, Hokkaido University

Abstract

<jats:title>Abstract</jats:title> <jats:p>Enzymatic epoxidation represents a key biosynthetic transformation in the construction of polyether skeletons. A single flavin-containing monooxygenase, Lsd18, is involved in ionophore polyether lasalocid biosynthesis and participates in the enantioselective epoxidations of the diene precursor. Biotransformation studies utilizing structurally simplified monoolefin analogs with different substitution patterns revealed important structural requirements for the enantiofacial selectivity of Lsd18-catalyzed epoxidations. These results enabled us to propose a substrate binding model of Lsd18, which was applied to the biosynthesis of other polyethers.</jats:p>

Journal

  • Chemistry Letters

    Chemistry Letters 43 (11), 1779-1781, 2014-08-08

    Oxford University Press (OUP)

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