The structure of vacidin A, an aromatic heptaene macrolide antibiotic. II. Stereochemistry of the antibiotic.
On the basis of coupling constants and rotating frame nuclear Overhauser effect spectroscopy of vacidin A methoxycarbonylmethylamide, the stereochemistry of the antibiotic was established. The configuration of the aglycone was determined as (3R,7R,9R,11S,13S,15R,17S,18R,19S,21R, 36S,37R,38S). The aminosugar constituent of the antibiotic was identified as beta-(D)-mycosamine. The chiral center at C-41 remains to be assigned.
Sowiński
P
P
Department of Pharmaceutical Technology and Biochemistry Technical University of Gdańsk, Poland.
Gariboldi
P
P
Pawlak
J K
JK
Borowski
E
E
D000900:Anti-Bacterial Agents / Q000031:analogs & derivatives; D002174:Candicidin / Q000031:analogs & derivatives; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure
D000900:Anti-Bacterial Agents; D002174:Candicidin; C031985:vacidin A