功能性稀有单糖2,3-二氨基-D-甘露糖醛酸的合成  

Synthesis of Functional Rare Monosaccharide 2,3-Diamino-D-mannuronic Acids

作　　者：田光宗 谢苏晴 孙文斌 邹小鹏 胡静 尹健 TIAN Guangzong;XIE Suqing;SUN Wenbin;ZOU Xiaopeng;HU Jing;YIN Jiana(Jiangnan University,a.School of Biotechnology,Key Laboratory of Carbohydrate Chemistry and Biotechnology,Ministry of Education,Wuxi 214122,China;School of Medicine,Wuxi 214122,China;School of Life Sciences and Health Engineering,Wuxi 214122,China)

机构地区：[1]江南大学生物工程学院,糖化学与生物技术教育部重点实验室,江苏无锡214122 [2]江南大学医学院,江苏无锡214122 [3]江南大学生命科学与健康工程学院,江苏无锡214122

出　　处：《中国现代应用药学》2024年第22期3043-3052,共10页Chinese Journal of Modern Applied Pharmacy

基　　金：国家自然科学基金项目(22107037、22277042、22325803)。

摘　　要：目的合成2种功能性2,3-二氨基-D-甘露糖醛酸糖苷,为研究其构效关系及生物医学应用提供物质基础。方法以烯丙基D-阿洛糖苷为原料,经C3位S_(N)2叠氮基亲核取代、C6位羟基氧化得到关键中间体3-叠氮基-D-葡萄糖醛酸,然后经端基位连接臂组装、C2位叠氮基亲核取代、叠氮基还原以及氨基的选择性乙眯基和乙酰基修饰等反应制得2种目标产物。结果所有中间体和目标产物结构均经^(1)H-NMR、^(13)C-NMR和HRMS确证,产物纯度经HPLC检测>99.0%。结论2种功能性稀有糖苷的合成路线操作简便,目标产物纯度高,为后续其免疫活性研究提供物质基础。OBJECTIVE To synthesize two functional 2,3-diamino-D-mannuronic acid glycosides for investigating their structure-activity relationships and biomedical applications.METHODS Starting with allyl D-allose as the starting material,the key intermediate 3-azido-D-glucuronic acid was synthesized by performing a nucleophilic substitution of the S_(N)2 azide group at the C3 position and oxidizing the hydroxyl group at the C6 position.Subsequently,two target products were obtained by reactions involving linker assembly,nucleophilic substitution of the azide group at the C2 position,reduction of the azide group,and selective modification of the amino group through acetamidino and acetyl groups.RESULTS The structures of all intermediates and target products were confirmed using ^(1)H-NMR,^(13)C-NMR,and HRMS,with the products purity exceeding 99.0%as determined by HPLC.CONCLUSION The synthetic route for these two functional rare glycosides is straightforward and the resulting products exhibit high purity,laying a solid foundation for future investigations into their immunological activities.

关 键 词：2 3-二氨基-D-甘露糖醛酸 化学合成 1 2-顺式-糖苷键 亲核取代 

分 类 号：R914.5[医药卫生—药物化学]