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Synthesis and Immunological Studies of Oligosaccharides that Consist of the Repeating Unit of Streptococcus pneumoniae Serotype 3 Capsular Polysaccharide
Author(s) -
Xiong Chenghe,
Feng Shaojie,
Qiao Yin,
Guo Zhongwu,
Gu Guofeng
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800754
Subject(s) - glucuronic acid , streptococcus pneumoniae , polysaccharide , immunogenicity , oligosaccharide , toxoid , antibody , microbiology and biotechnology , chemistry , biochemistry , glycosylation , glycopeptide , antigen , biology , immunization , immunology , antibiotics
A highly convergent and efficient strategy was developed for the chemical synthesis of complex oligosaccharides of Streptococcus pneumoniae type 3 capsular polysaccharides that contain multiple glucuronic acid units. Once the oligoglucosides were efficiently and stereoselectively assembled, the designated glucose units were regioselectively oxidized to glucuronic acid in one step at the final synthetic stage, which helped avoid difficult glycosylations that involved glucuronic acid. The target oligosaccharides had a free amino group at the reducing terminus and varied caps at the non‐reducing terminus to enable further modification and structure–activity relationship studies. Immunological evaluations of the oligosaccharide–tetanus toxoid conjugates showed that they elicited robust T‐cell‐dependent immunoglobulin G antibody responses and that the sugar chain length had a major impact on their immunological properties. In particular, the penta‐ and hexasaccharides were identified as promising antigens for vaccine development.