A nitrous acid biosynthetic pathway for diazo group formation in bacteria

Nat Chem Biol. 2016 Feb;12(2):73-5. doi: 10.1038/nchembio.1991. Epub 2015 Dec 21.

Abstract

Although some diazo compounds have bioactivities of medicinal interest, little is known about diazo group formation in nature. Here we describe an unprecedented nitrous acid biosynthetic pathway responsible for the formation of a diazo group in the biosynthesis of the ortho-diazoquinone secondary metabolite cremeomycin in Streptomyces cremeus. This finding provides important insights into the biosynthetic pathways not only for diazo compounds but also for other naturally occurring compounds containing nitrogen-nitrogen bonds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azo Compounds / chemistry
  • Bacteria / metabolism*
  • Biosynthetic Pathways / genetics*
  • Chromatography, Liquid
  • Cyclohexanones / chemistry
  • Diazonium Compounds / chemistry*
  • Genetic Engineering
  • Molecular Structure
  • Multigene Family / genetics
  • Nitrous Acid / chemistry*
  • Nitrous Acid / metabolism*

Substances

  • Azo Compounds
  • Cyclohexanones
  • Diazonium Compounds
  • cremeomycin
  • Nitrous Acid

Associated data

  • PubChem-Substance/255348104
  • PubChem-Substance/255348105
  • PubChem-Substance/255348106
  • PubChem-Substance/255348107
  • PubChem-Substance/255348108