title: Synthesis of Cholesterol-Substituted Glycopeptides for Tailor-Made Glycocalyxification of Artificial Membrane Systems.
abstract: Synthetic minimal membrane systems are extremely useful for better understanding of complex cellular structures and cell surface processes. We have developed a facile method for synthesis of cholesterylated peptides, each bearing a carbohydrate moiety and a fluorescent tag. The position of the cholesterol moiety on the peptide can be controlled by using a new Fmoc-protected cholesterol-triazole-lysine group, which we constructed by means of 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.
authors.affiliation: Department of Chemistry, Chemical Biology, University of Copenhagen, Thorvaldsensvej 40, 1871, Frederiksberg C, Denmark.
authors.forename: Nicolai
authors.initials: N
authors.lastname: Stuhr-Hansen
authors.affiliation: Albert-Ludwigs-University Freiburg, Faculty of Biology, Centre for Biological Signalling Studies (BIOSS) and, Freiburg Centre for Interactive Materials and Bioinspired Technology (FIT), Schänzlestrasse 18, 79104, Freiburg, Germany.
authors.forename: Josef
authors.identifier: 0000-0003-3637-2546
authors.initials: J
authors.lastname: Madl
authors.affiliation: Albert-Ludwigs-University Freiburg, Faculty of Biology, Centre for Biological Signalling Studies (BIOSS) and, Freiburg Centre for Interactive Materials and Bioinspired Technology (FIT), Schänzlestrasse 18, 79104, Freiburg, Germany.
authors.forename: Sarah
authors.identifier: 0000-0002-9671-036X
authors.initials: S
authors.lastname: Villringer
authors.affiliation: Department of Chemistry, Chemical Biology, University of Copenhagen, Thorvaldsensvej 40, 1871, Frederiksberg C, Denmark.
authors.forename: Ulrika
authors.initials: U
authors.lastname: Aili
authors.affiliation: Albert-Ludwigs-University Freiburg, Faculty of Biology, Centre for Biological Signalling Studies (BIOSS) and, Freiburg Centre for Interactive Materials and Bioinspired Technology (FIT), Schänzlestrasse 18, 79104, Freiburg, Germany.
authors.forename: Winfried
authors.identifier: 0000-0002-2847-246X
authors.initials: W
authors.lastname: Römer
authors.affiliation: Department of Chemistry, Chemical Biology, University of Copenhagen, Thorvaldsensvej 40, 1871, Frederiksberg C, Denmark. olablixt@chem.ku.dk.
authors.forename: Ola
authors.identifier: 0000-0003-4143-6276
authors.initials: O
authors.lastname: Blixt
mesh_terms: D002784:Cholesterol / Q000737:chemistry*; D019276:Glycocalyx / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D037102:Lectins / Q000378:metabolism; D008567:Membranes, Artificial; D060327:Solid-Phase Synthesis Techniques / Q000379:methods; D053835:Unilamellar Liposomes / Q000737:chemistry / Q000378:metabolism
chemical_list: D006020:Glycopeptides; D037102:Lectins; D008567:Membranes, Artificial; D053835:Unilamellar Liposomes; D002784:Cholesterol
keywords: glycocalyxs; glycopeptides; glycosylation; lectins; vesicles