Structure and total synthesis of fungal calpinactam, a new antimycobacterial agent.

Org Lett

Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.

Published: February 2010

AI Article Synopsis

  • A new fungal metabolite called calpinactam was isolated from Mortierella alpina FKI-4905, and its structure was determined using NMR and other spectroscopic methods.
  • Calpinactam is identified as a hexapeptide with a unique caprolactam ring at the end of its structure.
  • The compound showed significant selective inhibition of mycobacteria, with minimum inhibitory concentration (MIC) values of 0.78 µg/mL for Mycobacterium smegmatis and 12.5 µg/mL for M. tuberculosis.

Article Abstract

A new fungal metabolite designated calpinactam (1) was isolated from the culture broth of Mortierella alpina FKI-4905, and its structure was elucidated by spectroscopic analyses including NMR experiments. Calpinactam was found to be a hexapeptide with a caprolactam ring at its C-terminal. Its absolute stereochemistry was determined by amino acid analysis and total synthesis. Calpinactam selectively inhibited the growth of mycobacteria among various microorganisms. The MIC values of calpinactam against Mycobacterium smegmatis and M. tuberculosis were 0.78 and 12.5 microg/mL, respectively.

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Source
http://dx.doi.org/10.1021/ol902553zDOI Listing

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