Synthesis and structure of two new mycolactones isolated from M. ulcerans subsp. shinshuense

Org Lett. 2012 Sep 7;14(17):4618-21. doi: 10.1021/ol302072b. Epub 2012 Aug 27.

Abstract

Two new mycolactones, mycolactones S1 and S2, were isolated from culture agar of Mycobacterium ulcerans subsp. shinshuense. Their structures were established in a three-step procedure: (1) probable structures were speculated from MS analysis; (2) candidates were synthesized; (3) HPLC profiles were established for identification of the natural products. Newly isolated mycolactones correspond to the "oxidized forms" of mycolactone A/B, the causative toxin of Buruli ulcer, isolated from Mycobacterium ulcerans.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Buruli Ulcer / etiology
  • Chromatography, High Pressure Liquid
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Molecular Structure
  • Mycobacterium ulcerans / chemistry*

Substances

  • Macrolides
  • mycolactone S1
  • mycolactone S2