褐藻胶寡糖甘露糖醛酸二糖的合成  

Synthesis of Alginate dimannuronate

作　　者：杨克宝[1] 李春霞[1] 王坤[1] 管华诗[1] 于广利[1] 

机构地区：[1]中国海洋大学医药学院海洋药物教育部重点实验室,山东省糖科学与糖工程重点实验室,山东青岛266003

出　　处：《中国海洋药物》2012年第6期1-9,共9页Chinese Journal of Marine Drugs

基　　金：海洋公益性行业科研专项基金(201005024);长江学者和创新团队发展计划(IRT0944);山东省科技发展计划(2011GSF11815);青岛市公共领域科技支撑计划项目(11-2-3-73-jh)资助

摘　　要：目的通过化学合成的手段进行褐藻胶中甘露糖醛酸二糖的合成。方法以甘露糖为起始原料,利用α-甘露糖基三氟甲磺酸酯中间体经SN2亲核取代反应直接构建β-甘露糖苷键,然后选择性的氧化6-位羟基得到甘露糖醛酸二糖苷。结果利用4,6位苄叉保护的甘露糖硫苷5作为糖基供体,高立体选择性的构建了β-(1,4)-甘露糖苷键,然后利用TEMPO/BAIB选择性的氧化6-位羟基得到了β-D-(1,4)-甘露糖醛酸二糖甲基苷15。结论该研究为下一步合成聚合度更高的系列褐藻胶寡糖及其衍生物提供了有效的合成策略和方法。Objective To prepare structure-well-defined alginate disaccharides by chemical synthesis method. Methods Starting from the D-mannose, the β-mannopyranoside was directly synthesized through α- mannosyl triflate under the mechanism of SN2 substitution. β-mannopyranoside was followed by selec- tive oxidation on 6-OH to give target compound mannuronic acid disaccharide. Results By using 4,6-di- O-benzylidene-protected 1-thio mannoside 5 as a glycosyl donor, the stereoselective/3-D-mannosylation protocol provided the/3-（1,4）-D-mannobiose derivative, which upon regioselective oxidation on 6-OH with TEMPO/BAIB yielded the corresponding methyl β-1,4-di-D-mannuronic acid 15. Conclusion The research provided method and protocols for the synthesis of more alginate oligosaccharides in the future.

关 键 词：褐藻胶 甘露糖醛酸二糖 寡糖合成 

分 类 号：R914[医药卫生—药物化学]