Synthesis of Fucoidan-Mimetic Glycopolymers with Well-Defined Sulfation Patterns via Emulsion Ring-Opening Metathesis...

The approach developed here offers distinct and well-defined glycopolymers for deciphering the biological roles of natural bioactive polysaccharides. Fucose monomers were chemically synthesized and decorated with specific sulfation patterns including unsulfate, monosulfate, disulfate, and trisulfate groups. The six fucoidan-mimetic glycopolymers (18-23) were successfully fabricated through microwave-assisted ring-opening metathesis polymerization (ROMP) in an emulsion system. The molecular weight (M_w), polydispersity index (PDI), and multiple functional groups were fully characterized by SEC-MALLS-RI and NMR spectroscopy. Three glycopolymers (19, 21, 23) associated with 2-O-sulfation exhibited better inhibitory effects on the H1N1 virus, while glycopolymers (19, 20) with monosulfate groups were more effective against the H3N2 virus. These findings would promote the development of novel anti-influenza A virus (IAV) drugs based on natural fucoidans.