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Diabetes 51:2833-2839, 2002
© 2002 by the American Diabetes Association, Inc.

Peroxynitrite Induces Formation of N{varepsilon}-(Carboxymethyl)Lysine by the Cleavage of Amadori Product and Generation of Glucosone and Glyoxal From Glucose

Novel Pathways for Protein Modification by Peroxynitrite

Ryoji Nagai1, Yuka Unno1,2, Miki Cristina Hayashi1, Shuichi Masuda2, Fumitaka Hayase3, Naohide Kinae2, and Seikoh Horiuchi1

1 Department of Biochemistry, Kumamoto University School of Medicine, Kumamoto, Japan
2 School of Food and Nutritional Sciences and Graduate School of Nutritional and Environmental Sciences, University of Shizuoka, Shizuoka, Japan
3 Department of Agricultural Chemistry, Meiji University, Kawasaki, Japan

Accumulation of advanced glycation end products (AGEs) on tissue proteins increases with pathogenesis of diabetic complications and atherosclerosis. Here we examined the effect of peroxynitrite (ONOO-) on the formation of N{varepsilon}-(carboxymethyl)lysine (CML), a major AGE-structure. When glycated human serum albumin (HSA; Amadori-modified protein) was incubated with ONOO-, CML formation was detected by both enzyme-linked immunosorbent assay and high-performance liquid chromatography (HPLC) and increased with increasing ONOO- concentrations. CML was also formed when glucose, preincubated with ONOO-, was incubated with HSA but was completely inhibited by aminoguanidine, a trapping reagent for {alpha}-oxoaldehydes. For identifying the aldehydes that contributed to ONOO--induced CML formation, glucose was incubated with ONOO- in the presence of 2,3-diaminonaphthalene. This experiment led to identification of glucosone and glyoxal by HPLC. Our results provide the first evidence that ONOO- can induce protein modification by oxidative cleavage of the Amadori product and also by generation of reactive {alpha}-oxoaldehydes from glucose.


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