Stereoselective synthesis of (2S,3S,4Z)-4-fluoro-1,3-dihydroxy-2-(octadecanoylamino)octadec-4-ene, [(Z)-4-fluoroceramide], and its phase behavior at the air/water interface.

ABSTRACT:

Background

Sphingolipids belong to the most important constituents of the membranes of eukaryotic cells. As intermediates in sphingolipid metabolism, sphingosine and its N-octadecanoyl-derivative, ceramide, exhibit a variety of biological functions. These compounds play a crucial role in many essential biological processes such as cell growth, cell differentiation, cell recognition and apoptosis. More specifically, sphingolipids are crucial e.g. for the function of the skin because they contribute to the formation of the water permeability barrier consisting of a highly organized multilaminar lipid matrix of free fatty acids, cholesterol and ceramides containing additional hydroxyl groups in the sphingosin part and longer fatty acid amide functions.

Results

In a short synthe

SUBMITTER: Nikolova GS 

PROVIDER: S-EPMC2486483 | biostudies-literature | 2008

REPOSITORIES: biostudies-literature