National Glycoengineering Research Center and Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University , 27 Shanda Nan Lu, Jinan 250100, China.
Department of Chemistry, University of Florida , 214 Leigh Hall, Gainesville, Florida 32611, United States.
Org Lett. 2016 Nov 4;18(21):5552-5555. doi: 10.1021/acs.orglett.6b02796. Epub 2016 Oct 19.
The first chemical synthesis of the heptasaccharide repeating unit of type V group B Streptococcus capsular polysaccharide (CPS) by a preactivation-based one-pot [2 + 1 + 4] glycosylation strategy is described. The synthetic efficiency was further improved by using diol glycosyl acceptors for regio-/stereoselective glycosylation reactions. The synthetic target contains a free amino group at the reducing end, facilitating additional regioselective elaboration. The results should be useful for synthetic and biological studies of related CPSs.
本文描述了通过基于预活化的一锅[2+1+4]糖苷化策略首次对 VB 型组链球菌荚膜多糖（CPS）的七糖重复单元进行化学合成。通过使用二醇糖基供体进行区域/立体选择性糖苷化反应，进一步提高了合成效率。该合成目标在还原端含有游离氨基，有利于进一步进行区域选择性修饰。这些结果对于相关 CPS 的合成和生物学研究应该是有用的。
