NRPS substrate promiscuity diversifies the xenematides

Org Lett. 2011 Oct 7;13(19):5144-7. doi: 10.1021/ol2020237. Epub 2011 Sep 2.

Abstract

Xenematide, a cyclic depsipeptide antibiotic produced by Xenorhabdus nematophila, had a candidate nonribosomal peptide synthetase (NRPS) with atypical features. Differential metabolite analysis between a mutant and wildtype validated that this stand-alone NRPS was required for xenematide production, and further analysis led to a series of new xenematide derivatives encoded by the same NRPS. Our results indicate that adenylation domain promiscuity and relaxed downstream processing in the X. nematophila NRPS provide a conduit for xenematide diversification.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Depsipeptides / chemistry*
  • Depsipeptides / metabolism
  • Molecular Sequence Data
  • Molecular Structure
  • Peptide Synthases / chemistry
  • Peptide Synthases / metabolism*
  • Sequence Alignment
  • Substrate Specificity

Substances

  • Depsipeptides
  • xenematide
  • Peptide Synthases