文献类型：期刊文献

英文题名：Synthesis and immunomodulatory activity of the sulfated tetrasaccharide motif of type B ulvanobiuronic acid 3-sulfate

作者：Zhang, Liangliang[1];Wang, Xiaotong[1];Hua, Qingting[1];Wang, Junchang[1];Liu, Jianwen[1];Yang, You[1]

机构：[1]East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab New Drug Design, 130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2020

卷号：18

期号：39

起止页码：7932

外文期刊名：ORGANIC & BIOMOLECULAR CHEMISTRY

收录：;EI(收录号：20204409428836);WOS:【SCI-EXPANDED(收录号:WOS:000579572100024)】；

基金：Financial support from the National Natural Science Foundation of China (21871081, 22071054) and the Fundamental Research Funds for the Central Universities (50321031916002, 22221818014) is gratefully acknowledged.

语种：英文

外文关键词：Gold compounds

摘要：Ulvan is a sulfated polysaccharide from green algae with potent antitumor, antiviral, and immunomodulatory activities. However, no chemical synthesis of ulvan saccharides has been reported to date. In this paper, we performed the first efficient synthesis of the unique sulfated tetrasaccharide motif of type B ulvanobiuronic acid 3-sulfate. Based on the gold(i)-catalyzed glycosylation with glycosyl ynenoates as donors, efficient construction of the challenging alpha-(1 -> 4)-glycosidic bonds between iduronic acid and rhamnose building blocks was achieved to afford the tetrasaccharide skeleton in a stereospecific manner. The synthetic sulfated tetrasaccharide was found to significantly improve the phagocytic activity of macrophage RAW264.7 cells.