Analogues of glycosphingolipids and glycerolipids suitable for conjugationto gold- and amino-functionalised surfaces

A general synthesis of analogues of natural lipids, (i.e. lactosylceramide, globotriasylceramide, and phosphatidylcholine) where one of the alkyl chai ns carries a terminal thiol- or carboxyl functionality, is described. The l ipids were prepared by N- or O-acylation of sphingosine or monoacylglycerol derivatives. These lipids are suitable for anchoring to gold- or amino-fun ctionalised surfaces, thus creating mimics of a cell membrane for use in th e study of protein-carbohydrate interaction. (C) 2000 Elsevier Science Ltd. All rights reserved.