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Synthesis of Cholesterol‐Substituted Glycopeptides for Tailor‐Made Glycocalyxification of Artificial Membrane Systems
Author(s) -
StuhrHansen Nicolai,
Madl Josef,
Villringer Sarah,
Aili Ulrika,
Römer Winfried,
Blixt Ola
Publication year - 2016
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201600258
Subject(s) - liposome , glycocalyx , moiety , membrane , artificial cell , peptide , glycopeptide , chemistry , vesicle , peptide synthesis , surface modification , combinatorial chemistry , lysine , amino acid , biochemistry , stereochemistry , antibiotics
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.