Chemical Synthesis of the Repeating Unit of Type V Group B Streptococcus Capsular Polysaccharide.
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.
National Glycoengineering Research Center and Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University , 27 Shanda Nan Lu, Jinan 250100, China.
Jian
J
Gao
Department of Chemistry, University of Florida , 214 Leigh Hall, Gainesville, Florida 32611, United States.
Zhongwu
Z
Guo
D016667:Bacterial Capsules / Q000737:chemistry*; D002236:Carbohydrate Conformation; D006031:Glycosylation; D013237:Stereoisomerism
C068312:capsular polysaccharide, streptoccal group B type V