Tetrodecamycin and dihydrotetrodecamycin, new antimicrobial antibiotics against Pasteurella piscicida produced by Streptomyces nashvillensis MJ885-mF8. II. Structure determination.
Novel antimicrobial antibiotics against Pasteurella piscicida, tetrodecamycin (1) and weakly active dihydrotetrodecamycin (2) were isolated from a culture broth of Streptomyces nashvillensis MJ885-mF8. The planar structure of 1 was determined to be 2-acyl-4-ylidene tetronic acid alkyl ether containing decaline ring by various NMR spectral data of 1 and its acetyl derivative (3). The structure of 2 was elucidated by comparison with the spectral data of 1 and confirmed by catalytic reduction of 1 into 2. The X-ray crystallography of 2 showed the relative stereochemistry. Their absolute configurations were determined by using modified Mosher's method.
D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D005663:Furans / Q000737:chemistry / Q000494:pharmacology; D008968:Molecular Conformation; D015394:Molecular Structure; D010325:Pasteurella / Q000187:drug effects; D013302:Streptomyces
D000900:Anti-Bacterial Agents; D005663:Furans; C096937:dihydrotetrodecamycin; C087129:tetrodecamycin