Open AccessSynthesis of Oligosaccharides Resembling the Streptococcus suis Serotype 18 Capsular Polysaccharide as a Basis for Glycoconjugate Vaccine Development
Author(s) -
Rajat Singh,
Julinton Sianturi,
Peter H. Seeberger
Publication year - 2022
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.2c00596
Subject(s) - glycoconjugate , polysaccharide , serotype , trisaccharide , chemistry , context (archaeology) , streptococcus suis , microbiology and biotechnology , pathogen , oligosaccharide , stereochemistry , biochemistry , biology , virulence , gene , paleontology
Here we report the first total synthesis of several oligosaccharides resembling the capsular polysaccharide of swine pathogen S. suis serotype 18 repeating unit [→3)-d-GalNAc(α1-3)[d-Glc(β1-2)]-d-GalA4OAc(β1-3)-d-GalNAc(α1-3)-d-BacNAc4NAc(α1→] n . Access to the pentasaccharide repeating unit antigen proved to be very challenging due to the poor reactivity in the context of the trisaccharide. The challenge was overcome by the creation of a galacturonic acid in a late stage of the synthesis.