Tanaka Tomonari, Ishitani Hideki, Miura Yoshiko, Oishi Kenta, Takahashi Tadanobu, Suzuki Takashi, Shoda Shin-Ichiro, Kimura Yoshiharu
Department of Biobased Materials Science, Graduate School of Science and Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan.
Department of Chemical Engineering, Graduate School of Engineering, Kyusyu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan.
ACS Macro Lett. 2014 Oct 21;3(10):1074-1078. doi: 10.1021/mz500555x. Epub 2014 Oct 6.
Glycopolymers having pendant triazole-linked sialyloligosaccharides were successfully synthesized from free saccharides without any protection of the hydroxy and carboxy groups on the saccharides. The glycomonomers were synthesized by the direct azidation of free saccharides using 2-chloro-1,3-dimethylimidazolinium chloride as a condensing agent followed by copper(I)-catalyzed azide-alkyne cycloaddition. The resultant glycomonomers were copolymerized with acrylamide by a reversible addition-fragmentation chain transfer technique. Each of the glycopolymers were obtained and then immobilized on a gold-coated sensor of quartz crystal microbalance to analyze their binding behavior with the lectin. The glycopolymers strongly bound with the corresponding lectin without nonspecific adsorption in aqueous solution. In addition, the glycopolymer bearing a complex-type sialyl N-linked oligosaccharide was found to strongly bind with both human and avian influenza A viruses. The strong binding, observed using the hemagglutination inhibition assay, was attributed to the glycocluster effect of the glycopolymer and the biantennary structure of the N-linked oligosaccharide.
具有侧链三唑连接唾液酸寡糖的糖聚合物已成功地从游离糖类合成，糖类上的羟基和羧基无需任何保护。糖单体通过使用2-氯-1,3-二甲基咪唑鎓氯化物作为缩合剂对游离糖类进行直接叠氮化，然后进行铜（I）催化的叠氮化物-炔烃环加成反应来合成。所得的糖单体通过可逆加成-断裂链转移技术与丙烯酰胺共聚。获得了每种糖聚合物，然后将其固定在石英晶体微天平的金涂层传感器上，以分析它们与凝集素的结合行为。这些糖聚合物在水溶液中与相应的凝集素强烈结合且无非特异性吸附。此外，发现带有复合型唾液酸N-连接寡糖的糖聚合物与人类和甲型禽流感病毒都能强烈结合。使用血凝抑制试验观察到的这种强结合归因于糖聚合物的糖簇效应和N-连接寡糖的双天线结构。
