Analogues of Glycosphingolipids and Glycerolipids Suitable for Conjugation to Gold- and Amino-Functionalised Surfaces

A general synthesis of analogues of natural lipids, (i.e. lactosylceramide, globotriasylceramide, and phosphatidylcholine) where one of the alkyl chains carries a terminal thiol- or carboxyl functionality, is described. The lipids were prepared by N- or O-acylation of sphingosine or monoacylglycerol derivatives. These lipids are suitable for anchoring to gold- or amino-functionalised surfaces, thus creating mimics of a cell membrane for use in the study of protein–carbohydrate interaction.