Synthesis of cholesterol-substituted glycopeptides for a tailor-made glycocalyxification of artificial membrane systems
Stuhr-Hansen N, Madl J, Villringer S, Aili U, Römer W, Blixt O.
For a better understanding of complex cellular structures and cell surface processes, synthetic minimal membrane systems are extremely useful. We developed a facile method for synthesis of cholesterylated peptides that carry a carbohydrate moiety and a fluorescent tag. The cholesterol position on the peptide can be controlled by using a novel Fmoc protected cholesterol-triazole-lysine group, which we constructed using solid-phase peptide synthesis. We succeeded in integrating the glyco-modules into Giant Unilamellar Vesicles by electroformation or infusion in buffer solution. The glyco-decorated liposomes were recognized by a lectin and had unique topological membrane features. In conclusion, this work is a proof of principle for the functionalization of artificial membranes with a primitive synthetic glycocalyx useful for studying carbohydrate-protein interactions on a simplified cell-like membrane surface.
