Reactivity and oxidative potential of fructose and glucose in enkephalin-sugar model systems

Amino Acids. 2008 Feb;34(2):329-32. doi: 10.1007/s00726-006-0488-6. Epub 2007 Feb 14.

Abstract

The reactions of Leu- and Met-enkephalin (Tyr-Gly-Gly-Phe-Leu/Met) with fructose resulted in the parallel formation of Heyns compounds (N-peptidyl-D-mannosamine and -D-glucosamine) and sugar-peptide generated imidazolidinone diastereomers. Glucose showed higher level of reactivity than fructose with respect to the extent of glycated product formation. The presence of fructose in the incubation mixtures makes Met residue more susceptible to oxidation than glucose.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Enkephalin, Leucine / chemistry*
  • Enkephalin, Methionine / chemistry*
  • Fructose / metabolism*
  • Glucose / metabolism*
  • Maillard Reaction
  • Oxidation-Reduction

Substances

  • Fructose
  • Enkephalin, Methionine
  • Enkephalin, Leucine
  • Glucose