Thiol-ene and thiol-yne-based synthesis of glycodendrimers as nanomolar inhibitors of wheat germ agglutinin.

Alkene and alkyne functional polyester-based dendrimers of generation 1 to 4 have been prepd. and reacted under free-radical conditions with 2-acetamido-2-deoxy-1-thio-$\beta$-D-glucose (GlcNAc-SH). As the alkene-dendrimers underwent the addn. of one thiyl radical per ene group whereas each yne group of alkyne-dendrimers was satd. by two thiyl radicals, a collection of glycodendrimers with glycan d. ranging from six to ninety-six GlcNAc per dendrimer was obtained. The recognition properties of the prepd. glycodendrimers toward the wheat germ agglutinin (WGA) were evaluated by enzyme-linked lectin assay (ELLA). The eight glycodendrimers were excellent ligands showing IC50 values in the nanomolar range and relative potencies per sugar unit up to 2.27 e6 when compared to monosaccharidic GlcNAc used as monovalent ref. [on SciFinder(R)]

Références

Titre
Thiol-ene and thiol-yne-based synthesis of glycodendrimers as nanomolar inhibitors of wheat germ agglutinin.
Type de publication
Article de revue
Année de publication
2014
Revue
J. Polym. Sci. Part A Polym. Chem.
Volume
52
Pagination
2422–2433
ISSN
0887-624X
Soumis le 12 avril 2018