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含有4,6 - 二硫酸模式的硫酸软骨素四糖结构的合成及其与糖胺聚糖结合蛋白相互作用的分析

Syntheses of chondroitin sulfate tetrasaccharide structures containing 4,6-disulfate patterns and analysis of their interaction with glycosaminoglycan-binding protein.

作者信息

Miyachi Kento, Wakao Masahiro, Suda Yasuo

机构信息

Department of Chemistry, Biotechnology, and Chemical Engineering, Graduate School of Science and Engineering, Kagoshima University, 1-21-40 Kohrimoto, Kagoshima 890-0065, Japan.

Department of Chemistry, Biotechnology, and Chemical Engineering, Graduate School of Science and Engineering, Kagoshima University, 1-21-40 Kohrimoto, Kagoshima 890-0065, Japan.

出版信息

Bioorg Med Chem Lett. 2015 Apr 1;25(7):1552-5. doi: 10.1016/j.bmcl.2015.02.011. Epub 2015 Feb 16.

DOI:10.1016/j.bmcl.2015.02.011
PMID:25752983
Abstract

Chondroitin sulfate tetrasaccharide ligand conjugates, namely GlcA-GalNAc6S-GlcA-GalNAc4S6S (CS-C+E) 1, GlcA2S-GalNAc6S-GlcA2S-GalNAc4S6S (CS-D+T) 2, GlcA-GalNAc4S6S-GlcA-GalNAc4S (CS-E+A) 3, GlcA-GalNAc4S6S-GlcA-GalNAc6S (CS-E+C) 4, and GlcA-GalNAc4S6S-GlcA-GalNAc4S6S (CS-E+E) 5, were systematically synthesized using a disaccharide building block 6. Synthesized CS tetrasaccharide structures were immobilized onto gold-coated chips to prepare array-type sugar chips, and the binding properties of protein were evaluated by surface plasmon resonance imaging biosensor. CS-D+T, CS-E+A, CS-E+C, and CS-E+E showed greater affinity for basic fibroblast growth factor than did other tetrasaccharides (CS-C+D, C+E, D+D).

摘要

硫酸软骨素四糖配体缀合物,即GlcA-GalNAc6S-GlcA-GalNAc4S6S(CS-C+E)1、GlcA2S-GalNAc6S-GlcA2S-GalNAc4S6S(CS-D+T)2、GlcA-GalNAc4S6S-GlcA-GalNAc4S(CS-E+A)3、GlcA-GalNAc4S6S-GlcA-GalNAc6S(CS-E+C)4和GlcA-GalNAc4S6S-GlcA-GalNAc4S6S(CS-E+E)5,使用二糖构建模块6进行了系统合成。将合成的硫酸软骨素四糖结构固定在金涂层芯片上以制备阵列型糖芯片,并通过表面等离子体共振成像生物传感器评估蛋白质的结合特性。与其他四糖(CS-C+D、C+E、D+D)相比,CS-D+T、CS-E+A、CS-E+C和CS-E+E对碱性成纤维细胞生长因子表现出更高的亲和力。

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