Facile triflic acid-catalyzed α-1,2-cis-thio glycosylations: scope and application to the synthesis of S-linked oligosaccharides, glycolipids, sublancin glycopeptides, and TN/TF antigens.
Facile triflic acid-catalyzed α-1,2-cis-thio glycosylations: scope and application to the synthesis of S-linked oligosaccharides, glycolipids, sublancin glycopeptides, and TN/TF antigens.
复制标题
简易三氟甲磺酸催化α-1,2-顺式硫代糖基化：S-连接寡糖、糖脂、sublancin 糖肽和 TN/TF 抗原合成的范围和应用。
DOI：
10.1039/c9sc04079j
复制
发表时间：
2019
期刊：
影响因子：
8.4
通讯作者：
Nguyen,HienM
中科院分区：
文献类型：
--
作者：
Zhu,Sanyong;Samala,Ganesh;Sletten,EricT;Stockdill,JenniferL;Nguyen,HienM
由于S-糖缀合物比O-糖苷缀合物具有更高的化学稳定性和酶抗性，因此S-糖缀合物的研究吸引了越来越多的兴趣。我们在这里报道了一种简便的方法来获得α-1，2-cis-S-连接的糖苷，使用三氟甲磺酸作为催化剂，以促进一系列硫醇与D-氨基葡萄糖、半乳糖胺、葡萄糖和半乳糖亲电体的糖基化。该方法可广泛应用于立体选择性合成S-连接糖肽、寡糖和糖脂，且产率高，α-选择性好。通过这种催化方法克服了与这些S-连接产物的制备相关的许多合成限制。
Studies of S-linked glycoconjugates have attracted growing interest because of their enhanced chemical stability and enzymatic resistance over O-glycoside counterparts. We here report a facile approach to access α-1,2-cis-S-linked glycosides using triflic acid as a catalyst to promote the glycosylation of a series of thiols with D-glucosamine, galactosamine, glucose, and galactose electrophiles. This method is broadly applicable for the stereoselective synthesis of S-linked glycopeptides, oligosaccharides and glycolipids in high yield and excellent α-selectivity. Many of the synthetic limitations associated with the preparation of these S-linked products are overcome by this catalytic method.