Cytochrome c catalyzes the in vitro synthesis of arachidonoyl glycine

Biochem Biophys Res Commun. 2008 Jan 11;365(2):322-7. doi: 10.1016/j.bbrc.2007.10.175. Epub 2007 Nov 5.

Abstract

Long chain fatty acyl glycines are an emerging class of biologically active molecules that occur naturally and produce a wide array of physiological effects. Their biosynthetic pathway, however, remains unknown. Here we report that cytochrome c catalyzes the synthesis of N-arachidonoyl glycine (NAGly) from arachidonoyl coenzyme A and glycine in the presence of hydrogen peroxide. The identity of the NAGly product was verified by isotope labeling and mass analysis. Other heme-containing proteins, hemoglobin and myoglobin, were considerably less effective in generating arachidonoyl glycine as compared to cytochrome c. The reaction catalyzed by cytochrome c in vitro points to its potential role in the formation of NAGly and other long chain fatty acyl glycines in vivo.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acyl Coenzyme A / chemistry*
  • Arachidonic Acids / chemical synthesis*
  • Catalysis
  • Cytochromes c / chemistry*
  • Enzyme Activation
  • Glycine / analogs & derivatives*
  • Glycine / chemical synthesis
  • Glycine / chemistry*
  • Hydrogen Peroxide / chemistry*
  • Substrate Specificity

Substances

  • Acyl Coenzyme A
  • Arachidonic Acids
  • N-arachidonylglycine
  • arachidonyl-coenzyme A
  • Cytochromes c
  • Hydrogen Peroxide
  • Glycine