title: Intriguing substrate tolerance of epoxide hydrolase Lsd19 involved in biosynthesis of the ionophore antibiotic lasalocid A.
abstract: Recently, we reported that the epoxide hydrolase Lsd19, the first enzyme shown to catalyze epoxide-opening cascades, can catalyze the conversion of a putative bisepoxide intermediate to polyether antibiotic lasalocid, which involves energetically disfavored 6-endo-tet cyclization of the epoxy alcohol. Here, we examined the substrate tolerance of Lsd19. Lsd19 accepts various substrate analogues differing in the left segment of lasalocid and epoxide stereochemistry to afford either THF-THP or THF-THF products with excellent regioselectivity.
authors.affiliation: Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Matsuura
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Shichijo
authors.forename: Atsushi
authors.initials: A
authors.lastname: Minami
authors.forename: Akira
authors.initials: A
authors.lastname: Migita
authors.forename: Hiroki
authors.initials: H
authors.lastname: Oguri
authors.forename: Mami
authors.initials: M
authors.lastname: Watanabe
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Tokiwano
authors.forename: Kenji
authors.initials: K
authors.lastname: Watanabe
authors.forename: Hideaki
authors.initials: H
authors.lastname: Oikawa
mesh_terms: D000900:Anti-Bacterial Agents / Q000096:biosynthesis* / Q000737:chemistry; D055162:Biocatalysis; D003500:Cyclization; D004851:Epoxide Hydrolases / Q000737:chemistry / Q000378:metabolism*; D007832:Lasalocid / Q000096:biosynthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D004851:Epoxide Hydrolases; D007832:Lasalocid