Biosynthetic origin of the rare nitroaryl moiety of the polyketide antibiotic aureothin: involvement of an unprecedented N-oxygenase

J Am Chem Soc. 2004 Mar 31;126(12):3694-5. doi: 10.1021/ja039328t.

Abstract

The antibiotic aureothin is a rare natural nitroaromatic compound produced by Streptomyces thioluteus. By labeling experiments, we demonstrate for the first time that p-nitrobenzoate (PNBA) serves as a polyketide synthase starter unit. Cloning, heterologous expression, and inactivation experiments reveal that this unusual primer is synthesized from p-aminobenzoate (PABA) by means of AurF, a novel N-oxygenase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / biosynthesis*
  • Anti-Bacterial Agents / chemistry
  • Chromones / chemistry
  • Chromones / metabolism*
  • Genes, Bacterial
  • Molecular Structure
  • Multigene Family
  • Mutagenesis
  • Nitrobenzoates / chemistry
  • Nitrobenzoates / metabolism*
  • Oxygenases / genetics
  • Oxygenases / metabolism*
  • Streptomyces / enzymology*
  • Streptomyces / genetics

Substances

  • Anti-Bacterial Agents
  • Chromones
  • Nitrobenzoates
  • Oxygenases
  • aureothin
  • 4-nitrobenzoic acid