Area for Molecular Function, Division of Material Science, Graduate School of Science and Engineering, Saitama University, Sakura, Saitama 338-8570, Japan.
Area for Molecular Function, Division of Material Science, Graduate School of Science and Engineering, Saitama University, Sakura, Saitama 338-8570, Japan; Medical Innovation Research Unit (MiU), Advanced Institute of Innovative Technology (AIIT), Saitama University, Sakura, Saitama 338-8570, Japan; Health Science and Technology Research Area, Strategic Research Center, Saitama University, Sakura, Saitama 338-8570, Japan.
Bioorg Med Chem Lett. 2024 Feb 1;99:129616. doi: 10.1016/j.bmcl.2024.129616. Epub 2024 Jan 10.
Fischer's glycoside synthesis was applied to linker precursor alcohols of two different lengths having appropriate alkane chains to obtain the corresponding α-glycoside and it was found to be applicable with moderate yields. Water-soluble glycomonomers were systematically prepared from N-acetyl-d-glucosamine (GlcNAc) by introducing two kinds of alcohols having different methylene lengths. Typical radical polymerizations of the glycomonomers with acrylamide as a modulator for control of the distance between carbohydrate residues in water in the presence of ammonium persulfate (APS)-N,N,N',N'-tetramethylethylenediamine (TEMED) gave a series of glycopolymers with various α-glycoside-type GlcNAc residue densities. Fluorometric analysis of the interaction of wheat germ agglutinin (WGA) with the glycopolymers was performed and the results showed unique binding specificities based on structural differences.
菲舍尔糖苷合成法被应用于具有适当烷链的两种不同长度的连接子前体醇，以获得相应的α-糖苷，并且发现其具有中等产率的适用性。通过向 N-乙酰基-d-葡萄糖胺 (GlcNAc) 中引入两种具有不同亚甲基长度的醇，系统地制备了水溶性糖单体。在过硫酸铵 (APS)-N，N，N'，N'-四甲基乙二胺 (TEMED) 的存在下，以丙烯酰胺作为调节剂控制水中碳水化合物残基之间的距离，典型的糖单体自由基聚合得到了一系列具有不同α-糖苷型 GlcNAc 残基密度的糖聚合物。对糖聚合物与麦胚凝集素 (WGA) 的相互作用进行了荧光分析，结果表明基于结构差异具有独特的结合特异性。
