Synthesis of Oligosaccharides Resembling the Streptococcus suis Serotype 18 Capsular Polysaccharide as a Basis for Glycoconjugate Vaccine Development

[Image: see text] 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 repe...

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Autores principales: Singh, Rajat Kumar, Sianturi, Julinton, Seeberger, Peter H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8981331/
https://www.ncbi.nlm.nih.gov/pubmed/35311265
http://dx.doi.org/10.1021/acs.orglett.2c00596
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author Singh, Rajat Kumar
Sianturi, Julinton
Seeberger, Peter H.
author_facet Singh, Rajat Kumar
Sianturi, Julinton
Seeberger, Peter H.
author_sort Singh, Rajat Kumar
collection PubMed
description [Image: see text] 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.
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spelling pubmed-89813312022-04-06 Synthesis of Oligosaccharides Resembling the Streptococcus suis Serotype 18 Capsular Polysaccharide as a Basis for Glycoconjugate Vaccine Development Singh, Rajat Kumar Sianturi, Julinton Seeberger, Peter H. Org Lett [Image: see text] 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. American Chemical Society 2022-03-21 2022-04-01 /pmc/articles/PMC8981331/ /pubmed/35311265 http://dx.doi.org/10.1021/acs.orglett.2c00596 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Singh, Rajat Kumar
Sianturi, Julinton
Seeberger, Peter H.
Synthesis of Oligosaccharides Resembling the Streptococcus suis Serotype 18 Capsular Polysaccharide as a Basis for Glycoconjugate Vaccine Development
title Synthesis of Oligosaccharides Resembling the Streptococcus suis Serotype 18 Capsular Polysaccharide as a Basis for Glycoconjugate Vaccine Development
title_full Synthesis of Oligosaccharides Resembling the Streptococcus suis Serotype 18 Capsular Polysaccharide as a Basis for Glycoconjugate Vaccine Development
title_fullStr Synthesis of Oligosaccharides Resembling the Streptococcus suis Serotype 18 Capsular Polysaccharide as a Basis for Glycoconjugate Vaccine Development
title_full_unstemmed Synthesis of Oligosaccharides Resembling the Streptococcus suis Serotype 18 Capsular Polysaccharide as a Basis for Glycoconjugate Vaccine Development
title_short Synthesis of Oligosaccharides Resembling the Streptococcus suis Serotype 18 Capsular Polysaccharide as a Basis for Glycoconjugate Vaccine Development
title_sort synthesis of oligosaccharides resembling the streptococcus suis serotype 18 capsular polysaccharide as a basis for glycoconjugate vaccine development
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8981331/
https://www.ncbi.nlm.nih.gov/pubmed/35311265
http://dx.doi.org/10.1021/acs.orglett.2c00596
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