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

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RECERCAT Home > Universitat de Barcelona > Química Inorgànica i Orgànica > Articles publicats en revistes (Química Inorgànica i Orgànica) > View document

To access the full text documents, please follow this link: http://hdl.handle.net/2445/110393

dc.contributor	Universitat de Barcelona
dc.contributor.author	Calderón i Almendro, Raquel
dc.contributor.author	Mercadal, Nerea
dc.contributor.author	Abad Saiz, José Luis
dc.contributor.author	Ariza Piquer, Xavier
dc.contributor.author	Delgado Cirilo, Antonio
dc.contributor.author	García Gómez, Jordi
dc.contributor.author	Rodríguez Ramírez, Aleix
dc.contributor.author	Fabriàs Domingo, Gemma
dc.date	2017-05-03T13:40:20Z
dc.date	2017-04-23
dc.date	2017-05-03T13:40:21Z
dc.date	info:eu-repo/date/embargoEnd/2018-04-23
dc.identifier.citation	0009-3084
dc.identifier.citation	671168
dc.identifier.uri	http://hdl.handle.net/2445/110393
dc.format	8 p.
dc.format	application/pdf
dc.language.iso	eng
dc.publisher	Elsevier B.V.
dc.relation	Versió postprint del document publicat a: https://doi.org/10.1016/j.chemphyslip.2017.04.008
dc.relation	Chemistry and Physics of Lipids, 2017, vol. 205, p. 34-41
dc.relation	https://doi.org/10.1016/j.chemphyslip.2017.04.008
dc.rights	cc-by-nc-nd (c) Elsevier B.V., 2017
dc.rights	info:eu-repo/semantics/embargoedAccess
dc.rights	http://creativecommons.org/licenses/by-nc-nd/3.0/es
dc.subject	Esfingolípids
dc.subject	Síntesi orgànica
dc.subject	Estereoquímica
dc.subject	Enzimologia
dc.subject	Sphingolipids
dc.subject	Organic synthesis
dc.subject	Stereochemistry
dc.subject	Enzymology
dc.title	Stereoselective preparation of quaternary 2-vinyl sphingosines and ceramides and their effect on basal sphingolipid metabolism
dc.type	info:eu-repo/semantics/article
dc.type	info:eu-repo/semantics/acceptedVersion
dc.description.abstract	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.

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