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Synthesis and Immunological Studies of Oligosaccharides that Consist of the Repeating Unit of Streptococcus pneumoniae Serotype 3 Capsular Polysaccharide

Synthesis and Immunological Studies of Oligosaccharides that Consist of the Repeating Unit of... 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemistry - A European Journal Wiley

Synthesis and Immunological Studies of Oligosaccharides that Consist of the Repeating Unit of Streptococcus pneumoniae Serotype 3 Capsular Polysaccharide

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Publisher
Wiley
Copyright
© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
0947-6539
eISSN
1521-3765
DOI
10.1002/chem.201800754
pmid
29528515
Publisher site
See Article on Publisher Site

Abstract

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.

Journal

Chemistry - A European Journal – Wiley

Published: Jul 7, 2018

Keywords: ; ; ; ;

References