Format

Send to:

Choose Destination
See comment in PubMed Commons below
J Agric Food Chem. 2001 Mar;49(3):1493-501.

Isolation and characterization of glyoxal-arginine modifications.

Author information

  • 1Institute of Food Chemistry, Technical University of Berlin, Gustav-Meyer-Allee 25, TIB4/3-1, 13355 Berlin, Germany. marcus.glomb@tu-berlin.de

Abstract

5-(4,5-Dihydroxy-2-imino-1-imidazolidinyl)norvaline (1) was identified as the only product of the early reaction of arginine with glyoxal, which was slowly degraded to N(5)-[[(carboxymethyl)amino](imino)methyl]ornithine (3, N(7)-carboxymethylarginine). No other structures could be detected within a range of pH 4-8 and 20-50 degrees C in reaction conditions. The rates of formation for both products increased with pH and temperature. In equilibrium, the vincinal diol groups of 1 were 86% trans configured. The formation of 1 was reversible, as could be shown by cis-trans isomerization of the separated isomers and by regeneration of arginine in the presence of the alpha-dicarbonyl trapping reagents, o-phenylenediamine and aminoguanidine. Both 1 and 3 were converted to 5-(2-imino-5-oxo-1-imidazolidinyl)norvaline (2) only under strong acidic conditions.

PMID:
11312885
[PubMed - indexed for MEDLINE]
PubMed Commons home

PubMed Commons

0 comments
How to join PubMed Commons

    Supplemental Content

    Full text links

    Icon for American Chemical Society
    Loading ...
    Write to the Help Desk