Identification by Synthesis: Imidacins, Urocanate-Derived Alkaloids from the Myxobacterium Stigmatella aurantiaca

Org Lett. 2024 Aug 2;26(30):6359-6363. doi: 10.1021/acs.orglett.4c02036. Epub 2024 Jul 22.

Abstract

Innovative discovery approaches such as genome-mining and metabolomics-inspired methods have reshaped the natural product research field, complementing traditional bioactivity-based screens and allowing hitherto unseen compounds to be uncovered from previously investigated producers. In line with these trends, we report here imidacins, a novel class of secondary metabolites specific to the myxobacterial genus Stigmatella. A combination of secondary metabolome analysis, genome-mining techniques, spectroscopic analysis, and finally total synthesis was used to allow structure elucidation. Imidacins are urocanate-derived aliphatic acids with an adjacent cyclopropane moiety, structural features unprecedented in natural products to date.

MeSH terms

  • Alkaloids / chemical synthesis
  • Alkaloids / chemistry
  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Biological Products / pharmacology
  • Cyclopropanes / chemical synthesis
  • Cyclopropanes / chemistry
  • Cyclopropanes / pharmacology
  • Molecular Structure
  • Myxococcales / chemistry
  • Stigmatella aurantiaca* / chemistry

Substances

  • Alkaloids
  • Biological Products
  • Cyclopropanes