1. Academic Validation
  2. Caprazamycins, novel lipo-nucleoside antibiotics, from Streptomyces sp. II. Structure elucidation of caprazamycins

Caprazamycins, novel lipo-nucleoside antibiotics, from Streptomyces sp. II. Structure elucidation of caprazamycins

  • J Antibiot (Tokyo). 2005 May;58(5):327-37. doi: 10.1038/ja.2005.41.
Masayuki Igarashi 1 Yoshiaki Takahashi Tetsuo Shitara Hikaru Nakamura Hiroshi Naganawa Toshiaki Miyake Yuzuru Akamatsu
Affiliations

Affiliation

  • 1 Microbial Chemistry Research Center, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan. igarashim@bikaken.or.jp
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.

Figures
Products
  • Cat. No.
    Product Name
    Description
    Target
    Research Area
  • HY-N10499
    Caprazamycin Core Structure