| 吕昌仑,苏凯强,李尧,等.一种岩藻糖基化硫酸软骨素三糖的合成[J].中国海洋药物,2020,39(6):1-11. |
| 一种岩藻糖基化硫酸软骨素三糖的合成 |
| Synthesis of Fucosylated Chondroitin Sulfate Trisaccharide |
| 投稿时间：2020-04-29 修订日期：2020-05-20 |
| DOI： |
| 中文关键词: 岩藻糖基化硫酸软骨素 三糖 硫酸化 |
| English Keywords:Fucosylated chondroitin sulfate Trisaccharide sulfation |
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| 中文摘要: |
| 目的 通过化学合成的方法制备结构确证的FCS寡糖以研究其作用机制及构效关系。方法 基于天然海参中FCS结构，从单糖砌块开始，通过线性合成策略进行FCS三糖化合物的合成。结果 从功能化的单糖砌块开始，以12步反应23%的总收率制备了岩藻糖3，4位硫酸化的FCS三糖重复单元β-D-GalNAc（4，6-diS）（1-4）［α-L-Fuc（3，4-diS）（1-3）］-β-D-GlcA-OMP。结论 在合成中，建立了选择性O-硫酸化以及立体选择性糖基化的保护基策略，同时以高产率实现了各砌块间的偶联，为FCS类寡糖的合成研究提供了参考。化合物结构经1H NMR，13C NMR和HR-MS（ESI）表征。 |
| English Summary: |
| To prepare structure-confirmed FCS oligosaccharides by chemical synthesis to study its mechanism of action and structure-activity relationship. Methods Based on the structure of FCS in natural sea cucumbers， starting from monosaccharide blocks， the synthesis of FCS trisaccharide compounds was carried out by a linear synthesis strategy. Results We synthesized an FCS trisaccharide repeat unit with 3，4-di-sulfo fucosyl residue，β-D-GalNAc(4，6-diS)(1-4)[α-L-Fuc(3，4-diS)(1-3)]-β-D-GlcA-OMP，in a total yield of 23% through 12 steps reaction，starting from the functionalized monosaccharide building blocks. Conclusion In the synthesis，the protective group strategy for selective O-sulfation and stereoselective glycosylation was established，and the coupling between the blocks was achieved in high yield. Our research work provided a reference for the synthesis of FCS-related oligosaccharides. The structures were characterized by 1H NMR，13C NMR and HR-MS(ESI)． |
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