Canadian Journal of Chemistry p. 1472 - 1482 (1997)
Update date:2022-09-26
Topics:
Meunier, Serge J.
Wu, Quigquan
Wang, Sho-Nong
Roy, Rene
Hyperbranched glycodendrimers containing sialic acid residues were synthesized in order to further understand the multivalency effect and its role in carbohydrate-protein interactions. Gallic acid 7 as trivalent core and oligoethylene glycol derivatives as hydrophilic spacers were used to scaffold the dendritic backbones. α-Thiosialoside 16 was conjugated onto N-chloroacetylated dendritic precursors 13, 14, and 26 by nucleophilic substitution to afford trivalent 17, 18, and nonavalent 27 sialodendrimers. Complete sugar deprotection furnished water-soluble α-thiosialodendrimers 21, 22, and 29, which were used in protein-binding studies. Turbidimetric analysis confirmed the strong potential of sialodendrimers 29 having nine readily accessible sialic acid residues to bind, cross-link, and precipitate two different lectins. Preliminary results indicated that nonavalent α-sialodendrimer 29 had a greater affinity towards dimeric wheat germ agglutinin (WGA) and the lectin from the slug Limax flavus (LFA) than the corresponding trivalent glycodendrimers 21 and 22.
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