Ceramides are sphingolipids that greatly stabilize ordered membrane domains (lipid rafts), and displace cholesterol from them. Ceramide-rich rafts have been implicated in diverse biological processes. Because ceramide analogues have been useful for probing the biological function of ceramide, and may have biomedical applications, it is important to characterize how ceramide structure affects membrane properties, including lipid raft stability and composition. In this report, fluorescence quenching assays were used to evaluate the effect of analogues of ceramide with different N-acyl chains or different sphingoid backbones on raft stability and sterol content. The effect of replacing 18 mol% of sphingomyelin (SM) with ceramide in vesicles composed of a 1:1 (mol:mol) mixture of SM and dioleoylphosphatidylcholine (DOPC), with or without 25 mol% sterol, was examined. In the absence of sterol, the thermal stability of the SM-rich ordered domains increased with ceramide N-acyl chain length in the order C2:0 approximately C6:0 approximately C8:0

Ceramide is the hydrophobic membrane anchor of glycosphingolipids, a vital component of the human skin, and a novel signaling substance. We give an overview of ceramide analogues that have been prepared to address biochemical questions related to the various functions of this lipid. We also discuss possible therapeutic applications. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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We report on the synthesis of a series of 3-C- methylceramide derivatives 2a,b, 12a,b, 13a,b, and 14a,b.

Key indicatorsSingle-crystal X-ray study T = 123 K Mean '(C±C) = 0.002 A Ê R factor = 0.034 wR factor = 0.090 Data-to-parameter ratio = 21.1 For details of how these key indicators were automatically derived from the article, see