Crocadepsins-Depsipeptides from the Myxobacterium Chondromyces crocatus Found by a Genome Mining Approach

ACS Chem Biol. 2018 Jan 19;13(1):267-272. doi: 10.1021/acschembio.7b00900. Epub 2017 Dec 28.

Abstract

Analysis of the genome sequence of the myxobacterium Chondromyces crocatus Cm c5 revealed the presence of numerous cryptic megasynthetase gene clusters, one of which we here assign to two previously unknown chlorinated metabolites by a comparative gene inactivation and secondary metabolomics approach. Structure elucidation of these compounds revealed a unique cyclic depsipeptide skeleton featuring β- and δ-amide bonds of aspartic acid and 3-methyl ornithine moieties, respectively. Insights into their biosynthesis were obtained by targeted gene inactivation and feeding experiments employing isotope-labeled precursors. The compounds were produced ubiquitously by the species Chondromyces crocatus and were found to inhibit the carbon storage regulator-RNA interaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspartic Acid / chemistry
  • Depsipeptides / chemistry
  • Depsipeptides / metabolism*
  • Gene Silencing
  • Genome, Bacterial
  • Genomics
  • Magnetic Resonance Spectroscopy
  • Metabolomics
  • Molecular Structure
  • Multigene Family
  • Myxococcales / genetics*
  • Myxococcales / metabolism

Substances

  • Depsipeptides
  • Aspartic Acid