2026-04-17T03:06:17Zhttps://recercat.cat/oai/request

oai:recercat.cat:2445/1103932025-12-04T21:43:20Zcom_2072_1057col_2072_478917col_2072_478933

00925njm 22002777a 4500 dc Calderón i Almendro, Raquel author Mercadal, Nerea author Abad Saiz, José Luis author Ariza Piquer, Xavier author Delgado Cirilo, Antonio author García Gómez, Jordi author Rodríguez Ramírez, Aleix author Fabriàs Domingo, Gemma author 2017-05-03T13:40:20Z 2018-04-23T22:01:15Z 2017-04-23 2017-05-03T13:40:21Z 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. Esfingolípids Síntesi orgànica Estereoquímica Enzimologia Sphingolipids Organic synthesis Stereochemistry Enzymology Stereoselective preparation of quaternary 2-vinyl sphingosines and ceramides and their effect on basal sphingolipid metabolism