Identification of N7-(1-carboxyethyl)-arginine, a novel posttranslational protein modification of arginine formed at high hydrostatic pressure

Ann N Y Acad Sci. 2005 Jun:1043:55-8. doi: 10.1196/annals.1333.006.

Abstract

An aqueous solution of Nalpha-acetylarginine (0.1 mol/L) and glucose (0.3 mol/L) in 0.5 mol/L 3-[N-morpholino]propanesulfonic acid (5 mL; pH 7.0) was incubated at 110 degrees C for 2 h with application of high hydrostatic pressure (HHP). After enzymic deacetylation, the arginine modifications formed were separated by ion exchange chromatography. Besides N5-(4,5-dihydro-4-methyl-5-oxo-1H-imidazol-2-yl)-L-ornithine, the novel arginine modification N7-(1-carboxyethyl)-arginine was identified based on NMR and LC/MS measurements and synthesis-in particular, in samples reacted at a pressure of 600 MPa. As compared to samples treated at normal pressure, both compounds were formed in higher amounts at increased pressure.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arginine / analogs & derivatives*
  • Arginine / chemistry
  • Arginine / metabolism
  • Glucose*
  • Hydrostatic Pressure
  • Protein Processing, Post-Translational*

Substances

  • N7-(1-carboxyethyl)arginine
  • Arginine
  • Glucose