Chemical Synthesis of an Octasaccharide Derivative Related to Group B Streptococcus Cell-Wall Polysaccharide
Chongzhen Sun
National Glycoengineering Research Center and Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 72 Binhai Road, Qingdao, Shandong, 266237 China
Search for more papers by this authorZhaojun Liu
National Glycoengineering Research Center and Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 72 Binhai Road, Qingdao, Shandong, 266237 China
Search for more papers by this authorWuxian Zeng
National Glycoengineering Research Center and Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 72 Binhai Road, Qingdao, Shandong, 266237 China
Search for more papers by this authorXiaolin Ma
National Glycoengineering Research Center and Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 72 Binhai Road, Qingdao, Shandong, 266237 China
Search for more papers by this authorGuirong Wang
National Glycoengineering Research Center and Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 72 Binhai Road, Qingdao, Shandong, 266237 China
Search for more papers by this authorCorresponding Author
Guofeng Gu
National Glycoengineering Research Center and Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 72 Binhai Road, Qingdao, Shandong, 266237 China
NMPA Key Laboratory for Quality Research and Evaluation of Carbohydrate-based Medicine, Shandong University, 72 Binhai Road, Qingdao, Shandong, 266237 China
E-mail: [email protected]Search for more papers by this authorChongzhen Sun
National Glycoengineering Research Center and Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 72 Binhai Road, Qingdao, Shandong, 266237 China
Search for more papers by this authorZhaojun Liu
National Glycoengineering Research Center and Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 72 Binhai Road, Qingdao, Shandong, 266237 China
Search for more papers by this authorWuxian Zeng
National Glycoengineering Research Center and Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 72 Binhai Road, Qingdao, Shandong, 266237 China
Search for more papers by this authorXiaolin Ma
National Glycoengineering Research Center and Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 72 Binhai Road, Qingdao, Shandong, 266237 China
Search for more papers by this authorGuirong Wang
National Glycoengineering Research Center and Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 72 Binhai Road, Qingdao, Shandong, 266237 China
Search for more papers by this authorCorresponding Author
Guofeng Gu
National Glycoengineering Research Center and Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 72 Binhai Road, Qingdao, Shandong, 266237 China
NMPA Key Laboratory for Quality Research and Evaluation of Carbohydrate-based Medicine, Shandong University, 72 Binhai Road, Qingdao, Shandong, 266237 China
E-mail: [email protected]Search for more papers by this authorComprehensive Summary
Group B Streptococcus (GBS) is the major pathogen that causes invasive infectious diseases in neonates and infants. The development of preventive and therapeutic strategies against GBS infection has been becoming the most pressing subject worldwide. Group B carbohydrate (GBC), the group B-specific polysaccharide that distinguishes GBS with other streptococci species, has been identified as an attractive antigen for diagnosis and vaccine development because of its highly conservative tetra-antennary structure. In this paper, a highly convergent [3 + 5] glycosylation strategy for efficient synthesis of an octasaccharide derivative related to GBC oligosaccharide unit II has been developed. In this synthesis, each glycosylation reaction was efficiently constructed with glycosyl imidates, especially trifluoroacetimidate, as donors, and each glycosidic bond was stereoselectively controlled via the neighboring group participation effect of acyl group on the 2-O-position of imidate donors or the solvent effect of Et2O. Furthermore, the aminoethylphosphate group was smoothly installed on the 6-O-position of d-glucitol residue using the phosphoramidite method. After global deprotection, the target octasaccharide was successfully obtained from d-glucitol in 29 steps with an overall yield of 1.37%. The free amino group installed on the aminoethylphosphate spacer of the target molecule enables its modification with functionalized biomolecules for further biological studies.
Supporting Information
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Appendix S1: Supporting Information |
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