Department of Life Science and Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Showa-ku, Nagoya, Aichi, 466-8555, Japan.
Carbohydr Polym. 2020 Jan 1;227:115105. doi: 10.1016/j.carbpol.2019.115105. Epub 2019 Sep 16.
β-1,3-Glucans are important as immunostimulating agents in living organisms. The multivalent binding of β-1,3-glucans to dectin-1, a cell surface receptor, activates immunological defenses. To study artificial immunostimulating agents, glycopolymers carrying β-1,3-glucan trisaccharides as artificial ligands were synthesized. The β-1,3-glucan trisaccharide, defined as an active unit of β-1,3-glucan, was constructed from D-glucose by glycosylation. A norbornene group was introduced as a polymerizable group into the trisaccharide derivative at the aglycone. The prepared endo/exo norbornene stereoisomers of the monomers were separated by silica gel chromatography and identified by NMR spectroscopy and mass spectrometry. The synthesized glycosyl monomers were polymerized and copolymerized with norbornene using 2 generation Hoveyda-Grubbs catalyst, deprotected, and purified by gel filtration to prepare water-soluble glycopolymers of varied compositions and high molecular weights. These polymers will have the potential for multivalent binding to dectin-1 to activate immune response and facilitate studies to understand the binding mechanisms of β-1,3-glucans with dectin-1.
β-1,3-葡聚糖作为生物体内的免疫刺激剂非常重要。β-1,3-葡聚糖与细胞表面受体 dectin-1 的多价结合激活了免疫防御。为了研究人工免疫刺激剂，携带β-1,3-葡聚糖三糖作为人工配体的糖聚合物被合成。β-1,3-葡聚糖三糖被定义为β-1,3-葡聚糖的活性单元，由糖苷化作用从 D-葡萄糖构建而成。在糖苷配基处将降冰片烯基团引入三糖衍生物中作为可聚合基团。通过硅胶色谱法将制备的单体的endo/exo 降冰片烯立体异构体分离，并通过 NMR 光谱和质谱鉴定。使用 2 代 Hoveyda-Grubbs 催化剂聚合和共聚合成的糖基单体、脱保护并通过凝胶过滤纯化以制备具有不同组成和高分子量的水溶性糖聚合物。这些聚合物将有可能与 dectin-1 进行多价结合以激活免疫反应，并促进研究以了解β-1,3-葡聚糖与 dectin-1 的结合机制。
