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 lipo-uridyl antibiotics, which have been discovered as specific inhibitors of a bacterial translocase.
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Igarashi, M., Takahashi, Y., Shitara, T. et al. Caprazamycins, Novel Lipo-nucleoside Antibiotics, from Streptomyces sp.. J Antibiot 58, 327–337 (2005). https://doi.org/10.1038/ja.2005.41
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DOI: https://doi.org/10.1038/ja.2005.41
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