Stereostructure of luminamicin, an anaerobic antibiotic, via molecular dynamics, NMR spectroscopy, and the modified Mosher method.
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.
Gouda
Hiroaki
H
School of Pharmaceutical Sciences, Kitasato University, Shirokane, Minato-ku, Tokyo 108-8641, Japan.
Sunazuka
Toshiaki
T
Ui
Hideaki
H
Handa
Masaki
M
Sakoh
Yusuke
Y
Iwai
Yuzuru
Y
Hirono
Shuichi
S
Omura
Satoshi
S
D000900:Anti-Bacterial Agents / Q000737:chemistry*; D001421:Bacteria, Anaerobic / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation
D000900:Anti-Bacterial Agents; D007783:Lactones; C047328:luminamicin