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

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 metaboli...

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Detalhes bibliográficos
Autores: 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
Tipo de documento: artigo
Estado:Versión aceptada para publicación
Data de publicação:2017
País:España
Recursos:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositório:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/110393
Acesso em linha:https://hdl.handle.net/2445/110393
Access Level:Acceso aberto
Palavra-chave:Esfingolípids
Síntesi orgànica
Estereoquímica
Enzimologia
Sphingolipids
Organic synthesis
Stereochemistry
Enzymology
Descrição
Resumo: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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