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J Biol Chem, Vol. 273, Issue 30, 18714-18719, July 24, 1998

Role of the Maillard Reaction in Aging of Tissue Proteins
ADVANCED GLYCATION END PRODUCT-DEPENDENT INCREASE IN IMIDAZOLIUM CROSS-LINKS IN HUMAN LENS PROTEINS

Elisabeth Brinkmann Frye, Thorsten P. Degenhardt, Suzanne R. Thorpe^§, and John W. Baynes^§

From the  Department of Chemistry and Biochemistry and the ^§ Department of Ophthalmology, University of South Carolina, Columbia, South Carolina 29208

Dicarbonyl compounds such as glyoxal and methylglyoxal are reactive dicarbonyl intermediates in the nonenzymatic browning and cross-linking of proteins during the Maillard reaction. We describe here the quantification of glyoxal and methylglyoxal-derived imidazolium cross-links in tissue proteins. The imidazolium salt cross-links, glyoxal-lysine dimer (GOLD) and methylglyoxal-lysine dimer (MOLD), were measured by liquid chromatography/mass spectrometry and were present in lens protein at concentrations of 0.02-0.2 and 0.1-0.8 mmol/mol of lysine, respectively. The lens concentrations of GOLD and MOLD correlated significantly with one another and also increased with lens age. GOLD and MOLD were present at significantly higher concentrations than the fluorescent cross-links pentosidine and dityrosine, identifying them as major Maillard reaction cross-links in lens proteins. Like the N-carboxy-alkyllysines N-(carboxymethyl)lysine and N-(carboxyethyl)lysine, these cross-links were also detected at lower concentrations in human skin collagen and increased with age in collagen. The presence of GOLD and MOLD in tissue proteins implicates methylglyoxal and glyoxal, either free or protein-bound, as important precursors of protein cross-links formed during Maillard reactions in vivo during aging and in disease.

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Copyright © 1998 by The American Society for Biochemistry and Molecular Biology, Inc.

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