Glyoxal formation by Fenton-induced degradation of carbohydrates and related compounds.
In this paper, we provide a systematic analysis of glyoxal (1) formation from a range of monosaccharides and related compounds, to determine their potential role as sources of this alpha-oxoaldehyde in vivo. Substrates were reacted with the Fenton reagent (Fe(2+)/EDTA/H(2)O(2)) and the mixtures were analyzed by HPLC using the 6-hydroxy-2,4,5-triaminopyrimidine fluorimetric assay. The rank order of hexoses and their derivatives as glyoxal sources was found to be fructose > glucose = mannose = galactose > glucose-6-phosphate > mannitol. Within the pentose group, arabinose and ribose gave the higher yields of 1 followed by deoxyribose and its adenine N-glycosides and ribulose. Among the tested substrates, three-carbon compounds, that is, trioses and glycerol, but not glyceraldehyde-3-phosphate, were by far the most effective sources of 1. The effects of H(2)O(2) and Fe(2+)/EDTA concentrations as well as of other metal ions were also investigated.
Manini
Paola
P
Department of Organic Chemistry and Biochemistry, University of Naples Federico II, Italy.
La Pietra
Paola
P
Panzella
Lucia
L
Napolitano
Alessandra
A
d'Ischia
Marco
M
D050260:Carbohydrate Metabolism; D002241:Carbohydrates / Q000737:chemistry*; D002412:Cations / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D006037:Glyoxal / Q000138:chemical synthesis* / Q000737:chemistry; D006601:Hexoses / Q000737:chemistry; D006861:Hydrogen Peroxide / Q000737:chemistry* / Q000494:pharmacology; D007501:Iron / Q000737:chemistry*; D007661:Ketoses / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction / Q000187:drug effects; D010429:Pentoses / Q000737:chemistry
D002241:Carbohydrates; D002412:Cations; C045076:Fenton's reagent; D006601:Hexoses; D007661:Ketoses; D010429:Pentoses; D006037:Glyoxal; D006861:Hydrogen Peroxide; D007501:Iron