Selektiv funktionalisierbare Glycopeptide und Glycodendrimere in biologischen Testsystemen
Glycopeptides and dendrimer-functionalized peptides were synthesized. These derivatives were labeled with ruthenium bipyridyl complexes and coupled with HIV-haptenes for utilisation in luminescence immunoassays. Solid phase peptide synthesis was carried out applying the Fmoc-solid phase strategy. In addition the synthesis of selectively functionalized AnX-type dendrimers is described. The coupling of peptides with dendritic residues as well as biotinylation of these compounds was performed in solution. The AnX-type dendrimers were coupled with mannose and fucose derivatives as biologically relevant carbohydrate epitopes and thus were converted into glycodendrimers. By this approach multivalent mannose and fucose clusters could be obtained to serve as oligosaccharide mimics. Fucose clusters were functionalized using alkyl and oligo ethylene glycol thioacetates. These compounds could be immobilized on gold surfaces in self assembled monolayers. N-glycosides were synthesized from anomeric azides by a modified Staudinger reaction. In doing so building blocks were obtained, which can be used for the synthesis of glycopeptido mimetics.