First synthesis of "Majoral-Type" glycodendrimers bearing covalently bound alpha-D-mannopyranoside residues onto a hexachlocyclotriphosphazene core.
A short and efficient strategy for the first synthesis of "Majoral-Type" multivalent glycodendrimers bearing covalently bound alpha-D-mannopyranosides onto a cyclotriphosphazene scaffold assembled using single-step Sonogashira and click chemistry is reported. New glycoclusters with valencies ranging from 6 to 18 and different epitope spatial arrangements were obtained. Cross-linking abilities of this series of glycodendrimers were evaluated with the model lectin from Canavalia ensiformis (Concanavalin A). The decameric mannoside 23, built around 19, was shown to be much faster in cross-linking the tetravalent lectin Concanavalin A than the positive control, which is the polysaccharide mannan from yeast. The new glycoconjugates reported may be promising tools as probes or effectors of biological processes involving multivalent carbohydrate-binding proteins.
Touaibia
Mohamed
M
Department of Chemistry, Université du Québec à Montréal, P.O. Box 8888, Succ. Centre-ville, Montréal, Québec, Canada H3C 3P8.
Roy
René
R
D032449:Canavalia / Q000378:metabolism; D002241:Carbohydrates / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D003432:Cross-Linking Reagents / Q000737:chemistry; D050091:Dendrimers / Q000737:chemistry; D000939:Epitopes / Q000737:chemistry; D037102:Lectins / Q000737:chemistry; D008358:Mannose / Q000737:chemistry*; D008956:Models, Chemical; D009391:Nephelometry and Turbidimetry / Q000379:methods; D010758:Phosphorus / Q000737:chemistry; D011485:Protein Binding; D011956:Receptors, Cell Surface / Q000737:chemistry
D002241:Carbohydrates; D003432:Cross-Linking Reagents; D050091:Dendrimers; D000939:Epitopes; D037102:Lectins; D011956:Receptors, Cell Surface; C055213:saccharide-binding proteins; D010758:Phosphorus; D008358:Mannose