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https://hdl.handle.net/2445/110393| 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 Estereoquímica Enzimologia Sphingolipids Organic synthesis Stereochemistry Enzymology |
| 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: https://doi.org/10.1016/j.chemphyslip.2017.04.008 |
| It is part of: | Chemistry and Physics of Lipids, 2017, vol. 205, p. 34-41 |
| URI: | https://hdl.handle.net/2445/110393 |
| Related resource: | https://doi.org/10.1016/j.chemphyslip.2017.04.008 |
| ISSN: | 0009-3084 |
| Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
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