On the reaction of glyoxal with proteins

Osmotic stress is accompanied by protein glycation inArabidopsis thaliana

“…Among them, N ε -(carboxymethyl)lysine (CML; van de Kerkhof et al , 2004), N ε -(carboxyethyl)lysine (CEL; Zhu et al , 2012), ɛ-(2′-formyl-5′-hydroxymethyl-pyrrolyl)-L-norleucine (pyrraline; Foerster and Henle, 2003), and glyceraldehyde-derived pyridinium (GLAP; Usui et al , 2007) are the best-characterized lysine-derived products. For arginine residues, Schwarzenbolz and coworkers described 1-(4-amino-4-carboxybutyl)-2-imino-5-oxo-imidazolidine (Glarg) formed in the reaction with glyoxal (Schwarzenbolz et al , 1997) and yielding N δ -carboxylethylarginine (CMA) under physiological conditions (Glomb and Lang, 2001). Methylglyoxal forms methylglyoxal-derived hydroimidazolones (MG-Hs) with N δ -(5-methyl-4-oxo-5-hydroimidazolinone-2-yl)-L-ornithine (MG-H1) as the major representative (Henle et al , 1994).…”

High‐Dose Thiamine Therapy Counters Dyslipidemia and Advanced Glycation of Plasma Protein in Streptozotocin‐Induced Diabetic Rats

“…Both hyperglycemia and hyperlipidemia may be sources of glycating agents and give rise to increased levels of AGEs and advanced lipoxidation end products (ALEs). Glyoxal is a potent glycating agent formed in both glycation and lipid peroxidation processes and can lead to the formation of the glycation adducts N ε ‐carboxymethyl‐lysine, the hydroimidazolone N δ ‐(5‐hydro‐4‐imidazolon‐2‐yl)ornithine (G‐H1), and N ω ‐carboxymethylarginine 16–20. Methylglyoxal is formed mainly from the degradation of triosephosphates and also by ketone body metabolism and threonine catabolism 21.…”

“…Methylglyoxal formation was also found in a model lipid peroxidation system 22. It is a potent glycating agent, forming mainly the hydroimidazolone N δ ‐(5‐hydro‐5‐methyl‐4‐imidazolon‐2‐yl)‐ornithine (MG‐H1) and usually approximately 10‐fold lower amounts of N ε ‐(1‐carboxyethyl)lysine 19,23. The concentrations of glyoxal‐ and methylglyoxal‐derived AGEs were increased in protein extracts of renal glomeruli, retina, and the sciatic nerve of STZ‐induced diabetic rats 19.…”

Identification of Nω-Carboxymethylarginine, a New Advanced Glycation Endproduct in Serum Proteins of Diabetic Patients: Possibility of a New Marker of Aging and Diabetes

“…It was then synthesized from L-arginine and glyoxal, and other similar glyoxalarginine derivatives were recently characterized [17,18]. ␣-NFC-1, one of the above derivatives, that was formed in vitro by the reaction of glucose or ribose and arginine [18], and have a chemical structure similar to CMA shown in Fig.…”