Synthesis and supramolecular characterization of a novel class of glycopyranosyl-containing amphiphiles

Frank Reichel, Annie M. Roelofsen, Hubertus P.M. Geurts, Sjerry J. Van Der Gaast, Martinus C. Feiters, Geert Jan Boons*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

A novel class of glycopeptidolipids is described, which potentially can be used as a novel antigen-delivery system. The compounds have been prepared by a combination of solid-supported and solution-based methods. The use of the orthogonally protected FmocLysDde derivative provided an opportunity to incorporate two different types lipids. It was found that the model compound 1 forms aggregates in aqueous media which can be described as rod or tubelike structures. The aggregates can be stabilized by topotactic photopolymerization. Studies on the structural analogues 2-5 revealed the effect of the carbohydrate, peptide, and lipid moiety on the aggregation properties. It is concluded that none of the structure elements can lay claim to be exclusively important for the formation of highly organized aggregates such as tubes, fibers, or helical ribbons from 1, but the presence of all of these structural elements afforded the most uniformly shaped extended structures.

Original languageEnglish
Pages (from-to)3357-3366
Number of pages10
JournalJournal of Organic Chemistry
Volume65
Issue number11
DOIs
Publication statusPublished - 2 Jun 2000
Externally publishedYes

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