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

Calderón i Almendro, RaquelMercadal, NereaAbad Saiz, José LuisAriza Piquer, XavierDelgado Cirilo, AntonioGarcía Gómez, JordiRodríguez Ramírez, AleixFabriàs Domingo, Gemma2017-05-032018-04-232017-04-230009-3084https://hdl.handle.net/2445/110393The 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.8 p.application/pdfengcc-by-nc-nd (c) Elsevier B.V., 2017http://creativecommons.org/licenses/by-nc-nd/3.0/esEsfingolípidsSíntesi orgànicaEstereoquímicaEnzimologiaSphingolipidsOrganic synthesisStereochemistryEnzymologyStereoselective preparation of quaternary 2-vinyl sphingosines and ceramides and their effect on basal sphingolipid metabolisminfo:eu-repo/semantics/article6711682017-05-03info:eu-repo/semantics/openAccess28445710