Isolation and characterization of a new advanced glycation endproduct of dehydroascorbic acid and lysine

Biochim Biophys Acta. 2003 Mar 17;1620(1-3):235-44. doi: 10.1016/s0304-4165(03)00002-3.

Abstract

Proteins are subject of posttranslational modification by sugars and their degradation products in vivo. The process is often referred as glycation. L-Dehydroascorbic acid (DHA), an oxidation product of L-ascorbic acid (vitamin C), is known as a potent glycation agent. A new product of modification of lysine epsilon -amino group by DHA was discovered as a result of the interaction between Boc-Lys and dehydroascorbic acid. The chromatographic and spectral analyses revealed that the structure of the product was 1-(5-ammonio-5-carboxypentyl)-3-oxido-4-(hydroxymethyl)pyridinium. The same compound was isolated from DHA modified calf lens protein after hydrolysis and chromatographic separation. The study confirmed that L-erythrulose is an important intermediate of modification of proteins by DHA. The structure of the reported product and in vitro experiments suggested that L-erythrulose could further transform to L-threose, L-erythrose and glycolaldehyde under conditions similar to physiological. The present study revealed that the modification of epsilon -amino groups of lysine residues by DHA is a complex process and could involve a number of reactive carbonyl species.

Publication types

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

MeSH terms

  • Acetaldehyde / analogs & derivatives*
  • Acetaldehyde / chemistry
  • Animals
  • Cattle
  • Chromatography, High Pressure Liquid
  • Dehydroascorbic Acid / chemistry*
  • Eye Proteins / chemistry
  • Glycation End Products, Advanced / chemical synthesis
  • Glycation End Products, Advanced / chemistry*
  • Glycation End Products, Advanced / isolation & purification
  • Lysine / analogs & derivatives*
  • Lysine / chemistry*
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Molecular Structure
  • Spectrometry, Mass, Electrospray Ionization
  • Tetroses / chemistry

Substances

  • Eye Proteins
  • Glycation End Products, Advanced
  • Tetroses
  • epsilon-tert-butyloxycarbonyl-lysine
  • erythrulose
  • Acetaldehyde
  • Lysine
  • glycolaldehyde
  • Dehydroascorbic Acid