Synthesis of 1,2-diacyl-sn-glycerophosphatidylserine from egg phosphatidylcholine by phosphoramidite methodology
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...
| Autores: | , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 1996 |
| País: | España |
| Institución: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositorio: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/141183 |
| Acceso en línea: | http://hdl.handle.net/10261/141183 |
| Access Level: | acceso abierto |
| Palabra clave: | 1,2 diacylglycerophosphatidylserine Gas Phosphatidylcholine Phospholipid Egg yolk Magnetic Resonance Spectroscopy |
| Sumario: | 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% 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. |
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