YS-822A, a new polyene macrolide antibiotic. II. Planar structure of YS-822A.
The planar structure of a new polyene macrolide antibiotic, YS-822A, which was isolated from the culture filtrate of a mutant strain H-8 of Streptoverticillium eurocidicum var. asterocidicus S-822, was established as I on the basis of spectroscopic evidences and by comparison spectroscopic data with nystatin A1 (II) and amphotericin A (III), representative polyene macrolide antibiotics. Molecular formula of YS-822A was established as C37H59NO14 (MW 741) by elemental analysis, NMR, and FAB mass spectra. The UV spectrum of YS-822A was very similar to that of nystatin A1, suggesting that YS-822A also has a conjugated all-trans-tetraene moiety. 1H and 13C NMR spectra of YS-822A showed a number of broad and overlapped signals, but the 1H-1H and 13C-1H COSY spectra implied the existence of a mycosamine moiety and several other partial structures. The connectivity of these partial structures was established by extensive 2D NMR experiments, including homonuclear Hartmann-Hahn and heteronuclear multiple-bond connectivity measurements, which led to the determination of the gross planar structure of YS-822A as I.
Hirota
H
H
Department of Chemistry, Faculty of Science, University of Tokyo, Japan.
Itoh
A
A
Ido
J
J
Iwamoto
Y
Y
Goshima
E
E
Miki
T
T
Hasuda
K
K
Ohashi
Y
Y
D000666:Amphotericin B / Q000031:analogs & derivatives / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000737:chemistry*; D000935:Antifungal Agents / Q000737:chemistry*; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009761:Nystatin / Q000737:chemistry; D013306:Streptomycetaceae / Q000737:chemistry
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D018942:Macrolides; C066092:YS 822A; D009761:Nystatin; C041989:amphotericin A; D000666:Amphotericin B