ALKYL AND PERFLUOROALKYL GLYCOLIPID-BASED SUPRAMOLECULAR ASSEMBLIES

New amphiphilic agents with single or double-chain hydrogenated and/or fluorinated hydrophobic tails have been synthesized from natural disa ccharides (lactose, maltose). The sugar moiety is intended to allow sp ecific targeting of cell membrane sugar receptors. The introduction of a peptide moiety (Gly, Gly-Gly or Lys) between the hydrophilic head a nd the hydrophobic tail allows the adjustment of the hydrophilic-lipop hilic balance (HLB). These amphiphiles are shown to form vesicles and other supramolecular assemblies readily. The morphology of these assem blies strongly depends on the component's molecular structure. Glycoli pids with a single fluorinated chain produced disk-like assemblies; th e double-tailed analogs led to multilayer vesicles. The impact of the amino acid linkage is considerable for the double-tailed compounds: mu ltilamellar vesicles were readily obtained when one glycine residue wa s interposed between the carbohydrate and the hydrophobic double tail. With a glycyl-glycine spacer unilamellar vesicles were formed. With l ysine, the glycolipid molecules formed mainly disk-like lamellar struc tures, tubules and helical superstructures along with a few vesicles.