Cytosporacin, a highly unsaturated polyketide: application of the ACCORD-ADEQUATE experiment to the structural determination of natural products.
Cytosporacin (1), a novel antibacterial polyketide containing naphthopyranone and isochromandione moieties, was isolated from the fermentation broth of the fungus Cytospora rhizophorae. A (1)H-detected ACCORD-ADEQUATE pulse sequence that distinguished (2)J(CH) from (3)J(CH) correlations provided critical information for structural determination. NOE studies established the relative configuration and revealed the presence of two rotamers. A biosynthetic (13)C-labeling experiment indicated that cytosporacin was derived from acetate origin.
He
Haiyin
H
Natural Products Research, Chemical Sciences, Wyeth Research, 401 North Middletown Road, Pearl River, New York 10965, USA. heh@wyeth.com
Janso
Jeffrey E
JE
Williamson
R Thomas
RT
Yang
Hui Y
HY
Carter
Guy T
GT
D000085:Acetates / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000302:isolation & purification; D001578:Benzopyrans / Q000737:chemistry* / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D004121:Dimethyl Sulfoxide; D005285:Fermentation; D007553:Isotope Labeling; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D012997:Solvents; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D000085:Acetates; D000900:Anti-Bacterial Agents; D001578:Benzopyrans; D012997:Solvents; C481901:cytosporacin; D004121:Dimethyl Sulfoxide