Cai Chao, Solakyildirim Kemal, Yang Bo, Beaudet Julie M, Weyer Amanda, Linhardt Robert J, Zhang Fuming
Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, Troy, New York 12180, USA.
Carbohydr Polym. 2012 Jan 4;87(1):822-829. doi: 10.1016/j.carbpol.2011.08.075.
Chondroitin sulfate-E (chondroitin-4, 6-disulfate) was prepared from chondroitin sulfate-A (chondroitin-4 - sulfate) by regioselective sulfonation, performed using trimethylamine sulfur trioxide in formamide under argon. The structure of semi-synthetic chondroitin sulfate-E was analyzed by PAGE, (1)H NMR, (13)C NMR, 2D NMR and disaccharide analysis and compared with natural chondroitin sulfate-E. Both semi-synthetic and natural chondroitin sulfate-E were each biotinylated and immobilized on BIAcore SA biochips and their interactions with fibroblast growth factors displayed very similar binding kinetics and binding affinities. The current semi-synthesis offers an economical approach for the preparation of the rare chondroitin sulfate-E from the readily available chondroitin sulfate-A.
硫酸软骨素 - E（软骨素 - 4,6 - 二硫酸酯）由硫酸软骨素 - A（软骨素 - 4 - 硫酸酯）通过区域选择性磺化制备，该磺化反应在氩气氛围下于甲酰胺中使用三甲胺三氧化硫进行。通过聚丙烯酰胺凝胶电泳（PAGE）、氢核磁共振（¹H NMR）、碳核磁共振（¹³C NMR）、二维核磁共振（2D NMR）和二糖分析对半合成硫酸软骨素 - E的结构进行了分析，并与天然硫酸软骨素 - E进行了比较。将半合成和天然硫酸软骨素 - E分别进行生物素化并固定在BIAcore SA生物芯片上，它们与成纤维细胞生长因子的相互作用表现出非常相似的结合动力学和结合亲和力。当前的半合成方法为从易于获得的硫酸软骨素 - A制备稀有的硫酸软骨素 - E提供了一种经济的途径。
