Recyclable fluorous-tag assisted two-directional oligosaccharide synthesis enabled by interrupted Pummerer reaction mediated glycosylation,Chemical Science

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Recyclable fluorous-tag assisted two-directional oligosaccharide synthesis enabled by interrupted Pummerer reaction mediated glycosylation
Chemical Science ( IF 7.6 ) Pub Date : 2022-06-22 , DOI: 10.1039/d2sc01700h
Lei Cai ₁ , Qi Chen ₁ , Jian Guo ₁ , Zhihua Liang ₁ , Dengxian Fu ₁ , Lingkui Meng ₁ , Jing Zeng ₁ , Qian Wan ₁

Affiliation

Herein, we report a novel fluorous-tag assisted two-directional oligosaccharide assembly strategy, which maintained the high coupling efficiency of solution-phase synthesis and featured the advantage of an easy purification process comparable to solid-phase synthesis. A well-designed fluorous tag was decorated on the latent anomeric leaving group in interrupted Pummerer reaction mediated (IPRm) glycosylation. The high efficiency of the in-solution phase glycosylation and the unique affinity of the fluorous tag towards polytetrafluoroethylene (PTFE) particles allowed flexible assembly from the reducing end to the non-reducing end and fast purification by PTFE-assisted filtration. Moreover, the fluorous-tagged latent anomeric leaving group could be activated by oxidation and cleaved by IPRm glycosylation, thus enabling the elongation of the carbohydrate chain from the non-reducing end to the reducing end as well as the recovery of the fluorous tag. The present two-directional synthetic strategy is used to assemble the repeating unit of Streptococcus pneumoniae type 14 capsular polysaccharide.

中文翻译：

通过中断的 Pummerer 反应介导的糖基化实现可回收的氟标签辅助双向寡糖合成

在此，我们报告了一种新型的荧光标记辅助双向寡糖组装策略，该策略保持了液相合成的高耦合效率，并具有与固相合成相媲美的简单纯化过程的优势。在中断的 Pummerer 反应介导 (IPRm) 糖基化中，在潜在异头离去基团上装饰了精心设计的氟标签。溶液相糖基化的高效率和氟标签对聚四氟乙烯 (PTFE) 颗粒的独特亲和力允许从还原端到非还原端的灵活组装，并通过 PTFE 辅助过滤实现快速纯化。此外，荧光标记的潜在异头离去基团可以通过氧化激活并通过 IPRm 糖基化裂解，从而使碳水化合物链从非还原端延伸到还原端以及氟标签的回收。目前的双向合成策略用于组装重复单元肺炎链球菌14型荚膜多糖。

更新日期：2022-06-22

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