Aldecalmycin, a new antimicrobial antibiotic from Streptomyces. II. Structure elucidation by NMR studies.
A new antibiotic, aldecalmycin (1) was isolated from the culture broth of Streptomyces sp. MJ147-72F6. The 1H and 13C NMR spectra of 1 were complicated due to the presence of a beta-ketoaldehyde moiety. Therefore, 1 was converted into an ethylene ketal derivative (2) and into a dihydroaldecalmycin (3). These derivatives gave assignable NMR spectra. The planar structure was elucidated by using 1H-1H COSY, 2D-HOHAHA, 1H-13C COSY and HMBC spectra of 2. The conformation of the decalin ring was elucidated by using ID-HOHAHA, NOE difference and NOESY spectra of 3. The geometry of double bond in the side chain was determined by NOE difference and NOESY spectra of 3.
Sawa
R
R
Institute of Microbial Chemistry, Tokyo, Japan.
Takahashi
Y
Y
Sawa
T
T
Naganawa
H
H
Takeuchi
T
T
D000900:Anti-Bacterial Agents / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011714:Pyrans / Q000737:chemistry
D000900:Anti-Bacterial Agents; D011714:Pyrans; C073564:aldecalmycin