Independent synthesis of aminophospholipid-linked Maillard products

Phospholipid-linked glycation products are supposed to play an important role in lipid oxidation in vivo. Independent syntheses and unequivocal structural characterization are reported for the phosphatidyl ethanolamine (PE)-derived Amadori compound 4-hydroxy-4-oxo-1-[(palmitoyloxy)methyl]-9-(2,3,4,5-tetrahydroxytetrahydro-2H-pyran-2-yl)-3,5-dioxa-8-aza-4 lambda(5)-phosphanon -1-yl palmitate, pyrrolecarbaldehyde 2-{[(2-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]ethoxy}(hydroxy)phosphoryl]oxy}-1-[(palmitoyloxy)methyl]ethyl palmitate, the carboxymethyl (CM) derivative 7-hydroxy-7,13-dioxo-10-(palmitoyloxy)-6,8, 12-trioxa-3-aza-7 lambda(5)-phosphaoctacosan-1-oic acid, and the carboxyethyl (CE) derivative 7-hydroxy-2-methyl-7, 13-dioxo-10-(palmitoyloxy)-6,8, 12-trioxa-3-aza-7 lambda(5)-phosphaoctacosan-1-oic acid. With these reference compounds, a liquid chromatography-mass spectrometry (LCMS) method for the determination of such PE-linked Maillard products has been developed. (C) 2000 Elsevier Science Ltd. All rights reserved.