Investigating the biosynthetic origin of the nitro group in pyrrolomycins

J Nat Prod. 2008 Nov;71(11):1923-6. doi: 10.1021/np800401h. Epub 2008 Nov 6.

Abstract

Feasible modes of introducing the nitro group into pyrrolomycin antibiotics were investigated based on incorporation of (15)N-labeled arginine and proline into dioxapyrrolomycin, produced by the actinomycete culture LL-F42248. Biosynthesis of nitrated pyrrolomycins was unaffected by the presence of nitric oxide synthase (NOS) inhibitors. The culture was able to grow in nitrogen-free (minimal) media and produce nitrated secondary metabolites. These results indicate that LL-F42248 is capable of fixing nitrogen.

MeSH terms

  • Actinomyces / metabolism*
  • Arginine / metabolism
  • Arginine / pharmacology
  • Atmosphere / chemistry
  • Molecular Structure
  • Nitric Oxide Synthase / antagonists & inhibitors*
  • Nitrogen / metabolism
  • Nitrogen Fixation / physiology*
  • Pyrroles / chemistry
  • Pyrroles / pharmacology
  • omega-N-Methylarginine / metabolism
  • omega-N-Methylarginine / pharmacology

Substances

  • Pyrroles
  • omega-N-Methylarginine
  • pyrrolomycin C
  • Arginine
  • Nitric Oxide Synthase
  • Nitrogen