Protecting-Group-Free Synthesis of Glycopolymers Bearing Sialyloligosaccharide and Their High Binding with the Influenza Virus.
Protecting-Group-Free Synthesis of Glycopolymers Bearing Sialyloligosaccharide and Their High Binding with the Influenza Virus.
复制标题
DOI：
10.1021/mz500555x
复制
发表时间：
2014-10
影响因子：
5.8
通讯作者：
Tomonari Tanaka;H. Ishitani;Y. Miura;Kenta Oishi;Tadanobu Takahashi;Takashi Suzuki;S. Shoda;Y. Kimura
中科院分区：
文献类型：
--
作者：
Tomonari Tanaka;H. Ishitani;Y. Miura;Kenta Oishi;Tadanobu Takahashi;Takashi Suzuki;S. Shoda;Y. Kimura
以游离糖为原料，成功地合成了具有悬垂三唑连接的唾液寡糖的糖共聚物，而糖上没有任何羟基和羧基的保护。以2-氯-1,3-二甲基咪唑氯化铵为缩合剂，通过铜催化叠氮-炔环加成，将游离糖直接叠氮化合成糖共聚体。所得糖单体通过可逆加成-断裂链转移技术与丙烯酰胺共聚。得到了每一种糖共聚物，然后将它们固定在石英晶体微天平上的包金传感器上，分析它们与凝集素的结合行为。该糖共聚物在水溶液中与相应的凝集素紧密结合，无非特异性吸附。此外，发现含有络合物型唾液酰基n -寡糖的糖共聚物与人类和禽流感病毒都有很强的结合。使用血凝抑制实验观察到的强结合归因于糖共聚物的糖簇效应和n -连接低聚糖的双天线结构。
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.