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

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.

journal_name

Chem Phys Lipids

authors

Calderón R,Mercadal N,Abad JL,Ariza X,Delgado A,Garcia J,Rodríguez A,Fabriàs G

doi

10.1016/j.chemphyslip.2017.04.008

subject

Has Abstract

pub_date

2017-06-01 00:00:00

pages

34-41

eissn

0009-3084

issn

1873-2941

pii

S0009-3084(17)30014-2

journal_volume

205

pub_type

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