Tanaka Tomonari, Takahashi Tadanobu, Suzuki Takashi
Department of Biobased Materials Science, Graduate School of Science and Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto, 606-8585, Japan.
Department of Biochemistry, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan.
Methods Mol Biol. 2016;1367:39-48. doi: 10.1007/978-1-4939-3130-9_4.
Typical synthetic methods for glycopolymers are laborious and require multistep processes, including protection and deprotection steps. Here we describe a facile protecting-group-free synthetic approach to glycopolymers bearing oligosaccharides from free saccharides by direct azidation and click chemistry methods, followed by reversible addition-fragmentation chain transfer polymerization. This method can be applied not only to mono- and disaccharides, but also to large biologically relevant oligosaccharides having sialic acids. Due to the glycocluster effect, the glycopolymers strongly bind with the corresponding lectin and influenza A virus, as analyzed by the quartz crystal microbalance method and hemagglutination inhibition assay.
典型的糖聚合物合成方法费力且需要多步过程，包括保护和脱保护步骤。在此，我们描述了一种简便的、无保护基团的合成方法，通过直接叠氮化和点击化学方法，从游离糖类合成带有寡糖的糖聚合物，随后进行可逆加成-断裂链转移聚合。该方法不仅可应用于单糖和二糖，还可应用于含有唾液酸的大型生物相关寡糖。通过石英晶体微天平法和血凝抑制试验分析发现，由于糖簇效应，这些糖聚合物与相应的凝集素和甲型流感病毒紧密结合。
