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Synthesis of oligosaccharides resembling the Streptococcus suis serotype 18 capsular polysaccharide as a basis for glycoconjugate vaccine development

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Singh,  Rajat Kumar
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Sianturi,  Julinton
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger,  Peter H.
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Singh, R. K., Sianturi, J., & Seeberger, P. H. (2022). Synthesis of oligosaccharides resembling the Streptococcus suis serotype 18 capsular polysaccharide as a basis for glycoconjugate vaccine development. Organic Letters, 24(12), 2371-2375. doi:10.1021/acs.orglett.2c00596.


Cite as: http://hdl.handle.net/21.11116/0000-000A-2BDB-0
Abstract
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.