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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
Keywords: Esfingolípids
Síntesi orgànica
Organic synthesis
Issue Date: 23-Apr-2017
Publisher: Elsevier B.V.
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.
Note: Versió postprint del document publicat a:
It is part of: Chemistry and Physics of Lipids, 2017, vol. 205, p. 34-41
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ISSN: 0009-3084
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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