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Título

Synthesis of 1,2-diacyl-sn-glycerophosphatidylserine from egg phosphatidylcholine by phosphoramidite methodology

AutorMorillo, Margarita; Sagristá, Maria Lluïsa; De Madariaga, María África; Eritja Casadellà, Ramón
Palabras clave1,2 diacylglycerophosphatidylserine
Gas
Phosphatidylcholine
Phospholipid
Egg yolk
Magnetic Resonance Spectroscopy
Fecha de publicación1996
EditorSpringer
CitaciónLipids 31(5): 541-546 (1996)
Resumensimple chemical method for the synthesis of 1,2-diacyl-sn- glycerophosphatidylserine (PS), with the same fatty acid composition in the sn-1 and sn-2 glycerol positions as egg phosphatidylcholine (PC), is described. PS synthesis was carried out by a phosphite-triester approach, using 2-cyanoethyl-N,N,N',N'-tetraisopropylphosphorodiamidite (phosphoramiditate) as the phosphorylating agent, for the formation of phosphate linkage between serine and diacylglycerol. 1,2-Diacylglycerol, obtained from PC hydrolysis by phospholipase C, was coupled with N-t-BOC-L- serinebenzhydryl ester phosphoramidite with tetrazole as catalyst. Phosphite- triester was oxidized to the corresponding phosphate-triester with 30% H2O2 in CH2Cl2. The cyanoethyl group was removed by addition of an Et3N/CH3CN/pyridine mixture, and trifluoroacetic acid was used to eliminate the protecting groups of O-(1,2-diacylglycero-3-phospho)-N-t-BOC- serinebenzhydril ester. Purified PS was identified by thin-layer chromatography, infrared, and 1H nuclear magnetic resonance.
Versión del editor10.1007/BF02522649
URIhttp://hdl.handle.net/10261/141183
DOI10.1007/BF02522649
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