Stereoselective preparation of quaternary 2-vinyl sphingosines and ceramides and their effect on basal sphingolipid metabolism
Raquel Calderón, Nerea Mercadal, José Luis Abad, Xavier Ariza, Antonio Delgado,* Jordi Garcia, Aleix Rodríguez, Gemma Fabriàs
* Departament de Farmacologia, Toxicologia i Química Terapèutica, Unitat de Química Farmacèutica
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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