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

作者:Suzuki Gaku; Minami Atsushi; Shimaya Mayu; Kodama Takeshi; Morimoto Yoshiki; Oguri Hiroki; Oikawa Hideaki*
来源:Chemistry Letters, 2014, 43(11): 1779-1781.
DOI:10.1246/cl.140721

摘要

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.

  • 出版日期2014-11-5