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

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Title:	Stereoselective preparation of quaternary 2-vinyl sphingosines and ceramides and their effect on basal sphingolipid metabolism
Author:	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
Other authors:	Universitat de Barcelona
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.
Subject(s):	-Esfingolípids -Síntesi orgànica -Estereoquímica -Enzimologia -Sphingolipids -Organic synthesis -Stereochemistry -Enzymology
Rights:	cc-by-nc-nd (c) Elsevier B.V., 2017 info:eu-repo/semantics/embargoedAccess http://creativecommons.org/licenses/by-nc-nd/3.0/es
Document type:	Article Article - Accepted version
Published by:	Elsevier B.V.
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