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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Detalles 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 recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2017
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/110393
Acceso en línea:https://hdl.handle.net/2445/110393
Access Level:acceso abierto
Palabra clave:Esfingolípids
Síntesi orgànica
Estereoquímica
Enzimologia
Sphingolipids
Organic synthesis
Stereochemistry
Enzymology
Descripción
Sumario: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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