A series of four sialic acid-containing hexavalent sulfoglycodendrimers (SGDs) were synthesized in excellent yields using an efficient strategy involving multiple microwave-mediated reactions. Four sugars, sialic acid, and the dimer through tetramer of α-2→8-linked oligosialic acid were added to an aminooxy-terminated hexavalent dendrimer core using a chemoselective oxime-forming reaction. This method resulted in substantial improvements in reaction time and product yields over previous methods. These multivalent glycopolymers were designed as potential topical agents for preventing the sexual transmission of HIV-1. While inactive against HIV-1, the SGDs were also not cytotoxic, opening a pathway for the further development of anti-HIV SGDs.
Keywords: Glycodendrimers; HIV-1; aminooxy; microscale thermophoresis; microwave synthesis; oligosialic acid; oxime; sialic acid.