Synthesis and Supramolecular Characterization of a Novel Class of Glycopyranosyl-Containing Amphiphiles

• Published in: Journal of organic chemistry 2000-06, Vol.65 (11), p.3357-3366
• Main Authors: Reichel, Frank, Roelofsen, Annie M, Geurts, Hubertus P. M, van der Gaast, Sjerry J, Feiters, Martinus C, Boons, Geert-Jan
• Format: Article
• Language: English
• Subjects: Bacterial Vaccines - chemistry; Carbohydrate Sequence; Freeze Etching; Freeze Fracturing; Lipopolysaccharides - chemistry; Magnetic Resonance Spectroscopy; Microscopy, Electron; Molecular Sequence Data; Monosaccharides - chemistry; Surface-Active Agents - chemistry; X-Ray Diffraction
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo991685s

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.