Carbohydrate carbonyl mobility--the key process in the formation of alpha-dicarbonyl intermediates.
Covalently cross-linked proteins are among the major modifications caused by the advanced Maillard reaction. In the present study, the formation pathway of the dideoxyosone N6-(2,3-dihydroxy-5,6-dioxohexyl)-L-lysine is shown. To elucidate the formation of this glucose-derived dideoxyosone D-lactose (O-beta-D-galp-(1-->4)-D-glcp) and D-glucose-6-phosphate were incubated with lysine in the presence of the trapping reagent o-phenylenediamine (OPD). Synthesis and unequivocal structural characterization were reported for the quinoxalines of the dideoxyosones N6-(5,6-dihydroxy-2,3-dioxohexyl)-L-lysine and N6-(2,3-dihydroxy-4,5-dioxohexyl)-L-lysine, respectively. Additionally, dicarbonyl compounds derived from D-erythrose, D-glycero-D-mannoheptose, and D-gluco-L-talooctose were synthesized and structurally characterized.
Reihl
Oliver
O
Institut für Lebensmittelchemie (170), Universität Hohenheim, Garbenstr. 28, D70593 Stuttgart, Germany.
Rothenbacher
Thorsten M
TM
Lederer
Markus O
MO
Schwack
Wolfgang
W
D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D003432:Cross-Linking Reagents / Q000737:chemistry*; D019298:Glucose-6-Phosphate / Q000737:chemistry*; D017127:Glycation End Products, Advanced / Q000737:chemistry; D006601:Hexoses / Q000737:chemistry / Q000302:isolation & purification; D007785:Lactose / Q000737:chemistry*; D008239:Lysine / Q000031:analogs & derivatives / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015416:Maillard Reaction; D008358:Mannose / Q000031:analogs & derivatives / Q000737:chemistry; D013058:Mass Spectrometry; D015394:Molecular Structure; D010655:Phenylenediamines / Q000737:chemistry; D011789:Quantum Theory; D011810:Quinoxalines / Q000138:chemical synthesis / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013780:Tetroses / Q000737:chemistry
D003432:Cross-Linking Reagents; D017127:Glycation End Products, Advanced; D006601:Hexoses; D010655:Phenylenediamines; D011810:Quinoxalines; D013780:Tetroses; D019298:Glucose-6-Phosphate; C034193:1,2-diaminobenzene; D007785:Lactose; D008239:Lysine; D008358:Mannose; C073321:erythrose