Stendomycin and Pantomycin Are Identical Natural Products: Preparation of a Functionalized Bioactive Analogue

J Org Chem. 2018 Jul 6;83(13):7303-7308. doi: 10.1021/acs.joc.8b00553. Epub 2018 May 18.

Abstract

The natural products pantomycin and stendomycin were both reported as antimicrobial agents. We demonstrate by gene cluster analysis, LC-MS analysis, and isolation that these polypeptides are identical, and we identify previously unknown congeners. We show that stendomycin can be chemically modified at its electrophilic dehydrobutyrine moiety yielding the first bioactive analogue of this natural product which can undergo additional functionalization. This compound may be a valuable starting point for molecular probe development, and we invite its distribution to the scientific community.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimicrobial Cationic Peptides
  • Biological Products / chemistry*
  • Candida / drug effects
  • Cell Line
  • Chromatography, Liquid / methods
  • Peptides / chemistry*
  • Rats
  • Tandem Mass Spectrometry / methods

Substances

  • Antimicrobial Cationic Peptides
  • Biological Products
  • Peptides
  • stendomycin
  • pantomycin