Synthesis of β-1,3-glucan mimics by β-1,3-glucan trisaccharyl monomer polymerization
Synthesis of β-1,3-glucan mimics by β-1,3-glucan trisaccharyl monomer polymerization
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β-1,3-葡聚糖三糖基单体聚合合成β-1,3-葡聚糖模拟物
DOI：
10.1016/j.carbpol.2019.115105
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发表时间：
2020
影响因子：
11.2
通讯作者：
Yamamura Hatsuo
中科院分区：
文献类型：
--
作者：
Miyagawa Atsushi;Yamamura Hatsuo
β-1,3-葡聚糖是生物体内重要的免疫刺激剂。β-1,3-葡聚糖与细胞表面受体dectin-1的多价结合激活免疫防御。为了研究人工免疫刺激剂，合成了以β-1,3-葡聚糖三糖为人工配体的糖共聚物。β-1,3-葡聚糖三糖是β-1,3-葡聚糖的活性单元，由d -葡萄糖通过糖基化构建而成。降冰片烯基团作为可聚合基团被引入到糖基上的三糖衍生物中。用硅胶色谱法分离了制备的/外冰片烯单体的立体异构体，并用核磁共振光谱和质谱法对其进行了鉴定。采用第二代Hoveyda-Grubbs催化剂将合成的糖基单体与降冰片烯进行聚合、共聚、脱保护、凝胶过滤纯化，制备出不同组成、高分子量的水溶性糖基共聚物。这些聚合物将具有与dectin-1多价结合激活免疫反应的潜力，并有助于研究β-1,3-葡聚糖与dectin-1的结合机制。
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 preparedendo/exonorbornene 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 2ndgeneration 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.