2016
DOI: 10.1002/cbic.201600258
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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 m… Show more

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Cited by 18 publications
(29 citation statements)
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“…S6 ). The latter is a tailor-made glycopeptide which was previously presented to integrate into GUVs to generate glycodecorated vesicles 32 .…”
Section: Resultsmentioning
confidence: 99%
“…S6 ). The latter is a tailor-made glycopeptide which was previously presented to integrate into GUVs to generate glycodecorated vesicles 32 .…”
Section: Resultsmentioning
confidence: 99%
“…To investigate the adhesion process, glycan-decorated vesicles can be implemented to mimic the glycocalyx layer of the cell surface. Stuhr-Hansen et al [136] reconstituted another component of the glycocalyx layer by integrating synthesized, cholesterol-anchored glycopeptides into GUVs and checked their accessibility with lectin binding.…”
Section: Assembly Of Prototissues By Protocell Cross-linking and Adhementioning
confidence: 99%
“… 10 Recently, more complex cholesterol-substituted glycopeptides have been integrated in the creation of protocells, mimicking the glycocalyx present in cell surfaces of living organisms. 11 , 12 …”
Section: Introductionmentioning
confidence: 99%