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...

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Detalles Bibliográficos
Autores: Morillo, Margarita, Sagristá, Maria Lluïsa, De Madariaga, María África, Eritja Casadellà, Ramón
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
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repository_id_str
spelling Synthesis of 1,2-diacyl-sn-glycerophosphatidylserine from egg phosphatidylcholine by phosphoramidite methodologyMorillo, MargaritaSagristá, Maria LluïsaDe Madariaga, María ÁfricaEritja Casadellà, Ramón1,2 diacylglycerophosphatidylserineGasPhosphatidylcholinePhospholipidEgg yolkMagnetic Resonance Spectroscopysimple 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.This work was supported by Grant No. PB86-0042 from C.I.C.Y.T. (Spain).Peer reviewedSpringer NatureComisión Interministerial de Ciencia y Tecnología, CICYT (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]201620161996info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/141183reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés10.1007/BF02522649Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1411832026-05-22T06:33:51Z
dc.title.none.fl_str_mv Synthesis of 1,2-diacyl-sn-glycerophosphatidylserine from egg phosphatidylcholine by phosphoramidite methodology
title Synthesis of 1,2-diacyl-sn-glycerophosphatidylserine from egg phosphatidylcholine by phosphoramidite methodology
spellingShingle Synthesis of 1,2-diacyl-sn-glycerophosphatidylserine from egg phosphatidylcholine by phosphoramidite methodology
Morillo, Margarita
1,2 diacylglycerophosphatidylserine
Gas
Phosphatidylcholine
Phospholipid
Egg yolk
Magnetic Resonance Spectroscopy
title_short Synthesis of 1,2-diacyl-sn-glycerophosphatidylserine from egg phosphatidylcholine by phosphoramidite methodology
title_full Synthesis of 1,2-diacyl-sn-glycerophosphatidylserine from egg phosphatidylcholine by phosphoramidite methodology
title_fullStr Synthesis of 1,2-diacyl-sn-glycerophosphatidylserine from egg phosphatidylcholine by phosphoramidite methodology
title_full_unstemmed Synthesis of 1,2-diacyl-sn-glycerophosphatidylserine from egg phosphatidylcholine by phosphoramidite methodology
title_sort Synthesis of 1,2-diacyl-sn-glycerophosphatidylserine from egg phosphatidylcholine by phosphoramidite methodology
dc.creator.none.fl_str_mv Morillo, Margarita
Sagristá, Maria Lluïsa
De Madariaga, María África
Eritja Casadellà, Ramón
author Morillo, Margarita
author_facet Morillo, Margarita
Sagristá, Maria Lluïsa
De Madariaga, María África
Eritja Casadellà, Ramón
author_role author
author2 Sagristá, Maria Lluïsa
De Madariaga, María África
Eritja Casadellà, Ramón
author2_role author
author
author
dc.contributor.none.fl_str_mv Comisión Interministerial de Ciencia y Tecnología, CICYT (España)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv 1,2 diacylglycerophosphatidylserine
Gas
Phosphatidylcholine
Phospholipid
Egg yolk
Magnetic Resonance Spectroscopy
topic 1,2 diacylglycerophosphatidylserine
Gas
Phosphatidylcholine
Phospholipid
Egg yolk
Magnetic Resonance Spectroscopy
description 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.
publishDate 1996
dc.date.none.fl_str_mv 1996
2016
2016
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/141183
url http://hdl.handle.net/10261/141183
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv 10.1007/BF02522649
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Springer Nature
publisher.none.fl_str_mv Springer Nature
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,198674

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