title: Stereostructure of luminamicin, an anaerobic antibiotic, via molecular dynamics, NMR spectroscopy, and the modified Mosher method.
abstract: The absolute stereostructure of luminamicin, an anaerobic antibiotic, has been determined by using conformational analysis via high-temperature molecular dynamics, NMR spectroscopy, and the modified Mosher method. It was found that luminamicin has the S, S, R, R, R, R, S, S, S, R, and S configurations at C2, C4, C7, C9, C10, C11, C12, C13, C16, C28, and C29, respectively. This configuration is the same as that found in nodusmicin, which has a chemical structure quite similar to luminamicin. The structure of luminamicin consists of three different rings, i.e., a decalin ring, a 10-membered macrolactone ring, and a 14-membered macrolactone ring. The resulting three-dimensional structure of luminamicin shows an interesting feature in that the maleic anhydride functionality in conjugation with the enol ether group of the 14-membered macrolactone is nearly perpendicular to the plane of the other two rings.
authors.affiliation: School of Pharmaceutical Sciences, Kitasato University, Shirokane, Minato-ku, Tokyo 108-8641, Japan.
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Gouda
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Sunazuka
authors.forename: Hideaki
authors.initials: H
authors.lastname: Ui
authors.forename: Masaki
authors.initials: M
authors.lastname: Handa
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Sakoh
authors.forename: Yuzuru
authors.initials: Y
authors.lastname: Iwai
authors.forename: Shuichi
authors.initials: S
authors.lastname: Hirono
authors.forename: Satoshi
authors.initials: S
authors.lastname: Omura
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry*; D001421:Bacteria, Anaerobic / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation
chemical_list: D000900:Anti-Bacterial Agents; D007783:Lactones; C047328:luminamicin