title: Sequential enzymatic epoxidation involved in polyether lasalocid biosynthesis.
abstract: Enantioselective epoxidation followed by regioselective epoxide opening reaction are the key processes in construction of the polyether skeleton. Recent genetic analysis of ionophore polyether biosynthetic gene clusters suggested that flavin-containing monooxygenases (FMOs) could be involved in the oxidation steps. In vivo and in vitro analyses of Lsd18, an FMO involved in the biosynthesis of polyether lasalocid, using simple olefin or truncated diene of a putative substrate as substrate mimics demonstrated that enantioselective epoxidation affords natural type mono- or bis-epoxide in a stepwise manner. These findings allow us to figure out enzymatic polyether construction in lasalocid biosynthesis.
authors.affiliation: Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Minami
authors.forename: Mayu
authors.initials: M
authors.lastname: Shimaya
authors.forename: Gaku
authors.initials: G
authors.lastname: Suzuki
authors.forename: Akira
authors.initials: A
authors.lastname: Migita
authors.forename: Sandip S
authors.initials: SS
authors.lastname: Shinde
authors.forename: Kyohei
authors.initials: K
authors.lastname: Sato
authors.forename: Kenji
authors.initials: K
authors.lastname: Watanabe
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Tamura
authors.forename: Hiroki
authors.initials: H
authors.lastname: Oguri
authors.forename: Hideaki
authors.initials: H
authors.lastname: Oikawa
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000378:metabolism*; D003001:Cloning, Molecular; D004852:Epoxy Compounds / Q000737:chemistry / Q000378:metabolism*; D004987:Ethers / Q000737:chemistry / Q000378:metabolism; D007832:Lasalocid / Q000737:chemistry / Q000378:metabolism*; D010105:Oxygenases / Q000235:genetics / Q000378:metabolism*; D012240:Rhodococcus / Q000201:enzymology* / Q000235:genetics / Q000378:metabolism
chemical_list: D000900:Anti-Bacterial Agents; D004852:Epoxy Compounds; D004987:Ethers; D010105:Oxygenases; C020066:dimethylaniline monooxygenase (N-oxide forming); D007832:Lasalocid