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

• Gergana S. Nikolova and
• Günter Haufe

Beilstein J. Org. Chem. 2008, 4, No. 12, doi:10.3762/bjoc.4.12

• , 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

• 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 [23]. The function of the additional free OH group seems to be the

• -position. While the primary OH group is functionalized with a carbohydrate, a phosphate, sulfate, etc. the 3-OH group is free for various interactions with other constituents of the cell membrane such as cholesterol or proteins [1][26]. The nature of these interactions among other factors depends on the