Bi Jingjing, Zhao Chuanfang, Cui Wei, Zhang Chaoli, Shan Qiuli, Du Yuguo
State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China; School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100049, China.
School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100049, China.
Carbohydr Res. 2015 Aug 14;412:56-65. doi: 10.1016/j.carres.2015.05.001. Epub 2015 May 16.
Thioglycoside-containing trimannose analogs were designed and prepared to mimic the natural N-glycan core trisaccharide α-d-Man-(1→3)-[α-d-Man-(1→6)]-d-Man. (1→6)-S-Linked trimannoside 1 and its trivalent cluster 2 were synthesized in 11 and 15 steps, respectively, taking advantages of the armed mannopyranosyl trichloroacetimidate as glycosyl donor. Hemagglutination inhibition of the two new thiomannotriose analogs was preliminarily examined. Comparing to the parent trimannoside α-d-Man-(1→3)-[α-d-Man-(1→6)]-d-Man-OMe, the cluster mannotrioside 2 presented a comparable binding affinity to Con A, while the monomer 6-S-trimannoside 1 exhibited a slightly lower inhibition ability.
设计并制备了含硫代糖苷的三甘露糖类似物，以模拟天然N-聚糖核心三糖α-d-甘露糖-（1→3）-[α-d-甘露糖-（1→6）]-d-甘露糖。利用武装的吡喃甘露糖基三氯乙酰亚胺酯作为糖基供体，分别通过11步和15步合成了（1→6）-S-连接的三甘露糖苷1及其三价簇合物2。初步检测了这两种新型硫代甘露三糖类似物的血凝抑制作用。与母体三甘露糖苷α-d-甘露糖-（1→3）-[α-d-甘露糖-（1→6）]-d-甘露糖甲酯相比，簇状甘露三糖苷2对伴刀豆球蛋白A表现出相当的结合亲和力，而单体6-S-三甘露糖苷1的抑制能力略低。
