title: Caprazamycins, novel lipo-nucleoside antibiotics, from Streptomyces sp. II. Structure elucidation of caprazamycins.
abstract: 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.
authors.affiliation: Microbial Chemistry Research Center, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan. igarashim@bikaken.or.jp
authors.forename: Masayuki
authors.initials: M
authors.lastname: Igarashi
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Takahashi
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Shitara
authors.forename: Hikaru
authors.initials: H
authors.lastname: Nakamura
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Naganawa
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Miyake
authors.forename: Yuzuru
authors.initials: Y
authors.lastname: Akamatsu
mesh_terms: 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
chemical_list: D000904:Antibiotics, Antitubercular; D001381:Azepines; D014529:Uridine