A copper-containing oxidase catalyzes C-nitrosation in nitrosobenzamide biosynthesis

Nat Chem Biol. 2010 Sep;6(9):641-3. doi: 10.1038/nchembio.418. Epub 2010 Aug 1.

Abstract

Although C-nitroso aromatic compounds have several bioactivities of medicinal interest, the biosynthetic enzymes involved in C-nitrosation have remained unknown until now. Here, we report the entire biosynthesis pathway of 4-hydroxy-3-nitrosobenzamide in Streptomyces murayamaensis, in which a tyrosinase-like copper-containing monooxygenase is responsible for the C-nitrosation. This finding indicates diverse catalytic functions of tyrosinase-like copper-containing monooxygenases in nature.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzamides / chemistry
  • Benzamides / metabolism*
  • Biocatalysis
  • Copper / metabolism*
  • Mixed Function Oxygenases / chemistry
  • Mixed Function Oxygenases / metabolism
  • Nitrates / metabolism*
  • Nitrosation
  • Nitroso Compounds / chemistry
  • Nitroso Compounds / metabolism*
  • Oxidoreductases / chemistry
  • Oxidoreductases / metabolism*
  • Streptomyces / chemistry
  • Streptomyces / enzymology
  • Streptomyces / metabolism*

Substances

  • Benzamides
  • Nitrates
  • Nitroso Compounds
  • Copper
  • 3-nitrosobenzamide
  • Mixed Function Oxygenases
  • Oxidoreductases
  • copper oxidase

Associated data

  • PubChem-Substance/96107533
  • PubChem-Substance/96107534
  • PubChem-Substance/96107535
  • PubChem-Substance/96107536
  • PubChem-Substance/96107537
  • PubChem-Substance/96107538
  • PubChem-Substance/96107539
  • PubChem-Substance/96107540
  • PubChem-Substance/96107541
  • PubChem-Substance/96107542
  • PubChem-Substance/96107543
  • PubChem-Substance/96107544
  • PubChem-Substance/96107545
  • PubChem-Substance/96107546
  • PubChem-Substance/96107547