Preparation and characterization of glucosylated aminoglycerophospholipids.
Natural aminophospholipids were isolated from egg yolk and from human red blood cells. Glucosylated ethanolamine and serine phosphatides were prepared by exposing synthetic and natural aminophospholipids to glucose for 3-18 h at pH 7.4. The glucosylation products were resolved from parent phospholipids by normal-phase high-performance liquid chromatography and were identified by on-line mass spectrometry with an electrospray interface. The soft ionization method allowed us to detect the glucosylation products as molecular ions of the Schiff bases. The Schiff bases could be stabilized by sodium cyanoborohydride reduction. The molecular species of the ethanolamine and serine phosphatides reacted in proportion to their molar concentration in the mixtures. The yields of the glucosylation products varied with time of reaction and the concentration of glucose in the medium. At 50 mM glucose and 0.6 mg/mL phosphatidylethanolamine, 20% of the aminophospholipid was glycated in 18 h at 37 degrees C.
Banting and Best Department of Medical Research, University of Toronto, Ontario, Canada.
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Ravandi
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Kuksis
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Marai
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Myher
D001894:Borohydrides / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D004530:Egg Yolk / Q000737:chemistry; D004912:Erythrocytes / Q000737:chemistry; D005947:Glucose / Q000378:metabolism; D006031:Glycosylation; D006801:Humans; D006863:Hydrogen-Ion Concentration; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D010712:Phosphatidic Acids / Q000097:blood / Q000378:metabolism*; D010714:Phosphatidylethanolamines / Q000378:metabolism; D010718:Phosphatidylserines / Q000378:metabolism; D010743:Phospholipids / Q000378:metabolism; D012545:Schiff Bases
D001894:Borohydrides; D010712:Phosphatidic Acids; D010714:Phosphatidylethanolamines; D010718:Phosphatidylserines; D010743:Phospholipids; D012545:Schiff Bases; C009282:sodium cyanoborohydride; D005947:Glucose