Journal
MAILLARD REACTION: RECENT ADVANCES IN FOOD AND BIOMEDICAL SCIENCES
Volume 1126, Issue -, Pages 235-240Publisher
WILEY-BLACKWELL
DOI: 10.1196/annals.1433.008
Keywords
kinetics; protein glycation; glycolaldehyde; side-chain protein models
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We have studied the reactivity of glycolaldehyde (GLA) with N-acetyl-Cys and N-acetyl-Phe-Lys at physiological conditions of pH and temperature. The reaction between the N-Ac-Phe-Lys and GLA was studied in the presence of NaCNBH3 and then by using high-performance liquid chromatography (HPLC)-UV/Vis. The reaction between N-Ac-Cys and GLA was followed by stopped-flow spectroscopy with UV/Vis detection. Both the reduced Schiff base and thiohemiacetal were identified by H-1-NMR and HPLC-mass spectrometry detection. The kinetic rate constant for the thiohemiacetal formation is four orders of magnitude higher than that for the Schiff base formation. This result suggests that the thiol group represents the most important target in protein glycation.
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