Stereoselective preparation of quaternary 2-vinyl sphingosines and ceramides and their effect on basal sphingolipid metabolism

The dicyclohexylborane-mediated addition of allene 1 to (E)-2-tridecenal affords a quaternary protected 2-amino-2-vinyl-1,3-diol in good yield as a single diastereomer. This compound is readily transformed into the four stereoisomers of the quaternary (E)-2-vinyl analogs of sphingosine. The metaboli...

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Autores: Calderón i Almendro, Raquel, Mercadal, Nerea, Abad Saiz, José Luis, Ariza Piquer, Xavier, Delgado Cirilo, Antonio, García Gómez, Jordi, Rodríguez Ramírez, Aleix, Fabriàs Domingo, Gemma
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2017
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/110393
Acceso en línea:https://hdl.handle.net/2445/110393
Access Level:acceso abierto
Palabra clave:Esfingolípids
Síntesi orgànica
Estereoquímica
Enzimologia
Sphingolipids
Organic synthesis
Stereochemistry
Enzymology
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spelling Stereoselective preparation of quaternary 2-vinyl sphingosines and ceramides and their effect on basal sphingolipid metabolismCalderón i Almendro, RaquelMercadal, NereaAbad Saiz, José LuisAriza Piquer, XavierDelgado Cirilo, AntonioGarcía Gómez, JordiRodríguez Ramírez, AleixFabriàs Domingo, GemmaEsfingolípidsSíntesi orgànicaEstereoquímicaEnzimologiaSphingolipidsOrganic synthesisStereochemistryEnzymologyThe dicyclohexylborane-mediated addition of allene 1 to (E)-2-tridecenal affords a quaternary protected 2-amino-2-vinyl-1,3-diol in good yield as a single diastereomer. This compound is readily transformed into the four stereoisomers of the quaternary (E)-2-vinyl analogs of sphingosine. The metabolic fate and the effect of these compounds on the basal sphingolipid metabolism in human A549 lung adenocarcinoma cells has been studied, together with the ceramide analog of the most relevant vinylsphingosine derivative.Elsevier B.V.2017info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttps://hdl.handle.net/2445/110393Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésVersió postprint del document publicat a: https://doi.org/10.1016/j.chemphyslip.2017.04.008Chemistry and Physics of Lipids, 2017, vol. 205, p. 34-41https://doi.org/10.1016/j.chemphyslip.2017.04.008cc-by-nc-nd (c) Elsevier B.V., 2017http://creativecommons.org/licenses/by-nc-nd/3.0/esinfo:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1103932026-05-27T06:46:51Z
dc.title.none.fl_str_mv Stereoselective preparation of quaternary 2-vinyl sphingosines and ceramides and their effect on basal sphingolipid metabolism
title Stereoselective preparation of quaternary 2-vinyl sphingosines and ceramides and their effect on basal sphingolipid metabolism
spellingShingle Stereoselective preparation of quaternary 2-vinyl sphingosines and ceramides and their effect on basal sphingolipid metabolism
Calderón i Almendro, Raquel
Esfingolípids
Síntesi orgànica
Estereoquímica
Enzimologia
Sphingolipids
Organic synthesis
Stereochemistry
Enzymology
title_short Stereoselective preparation of quaternary 2-vinyl sphingosines and ceramides and their effect on basal sphingolipid metabolism
title_full Stereoselective preparation of quaternary 2-vinyl sphingosines and ceramides and their effect on basal sphingolipid metabolism
title_fullStr Stereoselective preparation of quaternary 2-vinyl sphingosines and ceramides and their effect on basal sphingolipid metabolism
title_full_unstemmed Stereoselective preparation of quaternary 2-vinyl sphingosines and ceramides and their effect on basal sphingolipid metabolism
title_sort Stereoselective preparation of quaternary 2-vinyl sphingosines and ceramides and their effect on basal sphingolipid metabolism
dc.creator.none.fl_str_mv Calderón i Almendro, Raquel
Mercadal, Nerea
Abad Saiz, José Luis
Ariza Piquer, Xavier
Delgado Cirilo, Antonio
García Gómez, Jordi
Rodríguez Ramírez, Aleix
Fabriàs Domingo, Gemma
author Calderón i Almendro, Raquel
author_facet Calderón i Almendro, Raquel
Mercadal, Nerea
Abad Saiz, José Luis
Ariza Piquer, Xavier
Delgado Cirilo, Antonio
García Gómez, Jordi
Rodríguez Ramírez, Aleix
Fabriàs Domingo, Gemma
author_role author
author2 Mercadal, Nerea
Abad Saiz, José Luis
Ariza Piquer, Xavier
Delgado Cirilo, Antonio
García Gómez, Jordi
Rodríguez Ramírez, Aleix
Fabriàs Domingo, Gemma
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Esfingolípids
Síntesi orgànica
Estereoquímica
Enzimologia
Sphingolipids
Organic synthesis
Stereochemistry
Enzymology
topic Esfingolípids
Síntesi orgànica
Estereoquímica
Enzimologia
Sphingolipids
Organic synthesis
Stereochemistry
Enzymology
description The dicyclohexylborane-mediated addition of allene 1 to (E)-2-tridecenal affords a quaternary protected 2-amino-2-vinyl-1,3-diol in good yield as a single diastereomer. This compound is readily transformed into the four stereoisomers of the quaternary (E)-2-vinyl analogs of sphingosine. The metabolic fate and the effect of these compounds on the basal sphingolipid metabolism in human A549 lung adenocarcinoma cells has been studied, together with the ceramide analog of the most relevant vinylsphingosine derivative.
publishDate 2017
dc.date.none.fl_str_mv 2017
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/110393
url https://hdl.handle.net/2445/110393
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: https://doi.org/10.1016/j.chemphyslip.2017.04.008
Chemistry and Physics of Lipids, 2017, vol. 205, p. 34-41
https://doi.org/10.1016/j.chemphyslip.2017.04.008
dc.rights.none.fl_str_mv cc-by-nc-nd (c) Elsevier B.V., 2017
http://creativecommons.org/licenses/by-nc-nd/3.0/es
info:eu-repo/semantics/openAccess
rights_invalid_str_mv cc-by-nc-nd (c) Elsevier B.V., 2017
http://creativecommons.org/licenses/by-nc-nd/3.0/es
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier B.V.
publisher.none.fl_str_mv Elsevier B.V.
dc.source.none.fl_str_mv Articles publicats en revistes (Química Inorgànica i Orgànica)
reponame:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,301603

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