Caprazamycins, novel lipo-nucleoside antibiotics, from Streptomyces sp. II. Structure elucidation of caprazamycins.
Novel antibiotics, active against acid-fast bacteria, caprazamycins, were isolated from the culture broth of Streptomyces sp. MK730-62F2. The planar structures of the compounds were determined by 2D NMR spectroscopic study. Furthermore, the absolute structure of caprazamycin B (2) was established by NMR spectroscopy and X-ray crystallography of its degradation products and by total synthesis of the 5-amino-5-deoxy-D-ribose moiety. In the course of degradation studies of 2 under alkaline and acidic conditions, we obtained the two core components, caprazene (11) and caprazol (14), respectively, in high yield. Structurally, caprazamycins belong to a family of lipouridyl antibiotics, which have been discovered as specific inhibitors of a bacterial translocase.
Igarashi
Masayuki
M
Microbial Chemistry Research Center, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan. igarashim@bikaken.or.jp
Takahashi
Yoshiaki
Y
Shitara
Tetsuo
T
Nakamura
Hikaru
H
Naganawa
Hiroshi
H
Miyake
Toshiaki
T
Akamatsu
Yuzuru
Y
D000818:Animals; D000904:Antibiotics, Antitubercular / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use; D001381:Azepines / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D018360:Crystallography, X-Ray; D051379:Mice; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013302:Streptomyces / Q000737:chemistry / Q000378:metabolism*; D014397:Tuberculosis, Pulmonary / Q000188:drug therapy* / Q000382:microbiology; D014529:Uridine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use
D000904:Antibiotics, Antitubercular; D001381:Azepines; D014529:Uridine