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Relative configuration of JBIR-129, a cytotoxic 34-membered glycosidic polyol macrolide from Streptomyces sp. RK74.

Authors
  • Kawahara, Teppei
  • Izumikawa, Miho
  • Takagi, Motoki
  • Shin-ya, Kazuo
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Sep 07, 2012
Volume
14
Issue
17
Pages
4434–4437
Identifiers
DOI: 10.1021/ol301940q
PMID: 22908979
Source
Medline
License
Unknown

Abstract

JBIR-129 was isolated as the potent cytotoxic compound, which consists of the 34-membered polyol macrolide skeleton with five sugar moieties. The relative configuration of the aglycone moiety (C7-C27 and C33-C39) was established by the J-based configuration analysis using vicinal (1)H-(1)H (from (1)H NMR and PS-DQF-COSY spectra) and long-range (1)H-(13)C coupling constants (from sge-HETLOC and several J-resolved HMBC spectra) with steric information obtained from ROESY.

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