Premium
Synthesis of 1,2‐diacyl‐ sn ‐glycerophosphadidylserine from egg phosphatidylcholine by phosphoramidite Methodology
Author(s) -
Morillo Margarita,
Sagristá M. Luisa,
Africa de Madariaga M.,
Eritja Ramón
Publication year - 1996
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02522649
Subject(s) - phosphoramidite , lipidology , phosphatidylcholine , chemistry , clinical chemistry , phospholipid , biochemistry , oligonucleotide , membrane , dna
A simple 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% H 2 O 2 in CH 2 Cl 2 . The cyanoethyl group was removed by addition of an Et 3 N/CH 3 CN/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 1 H nuclear magnetic resonance.