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  Chemical synthesis elucidates the immunological importance of a pyruvate modification in the capsular polysaccharide of Streptococcus pneumoniae serotype 4

Pereira, C. L., Geißner, A., Anish, C., & Seeberger, P. H. (2015). Chemical synthesis elucidates the immunological importance of a pyruvate modification in the capsular polysaccharide of Streptococcus pneumoniae serotype 4. Angewandte Chemie International Edition, 54(34), 10016-10019. doi:10.1002/anie.201504847.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0006-E9C3-7 Version Permalink: http://hdl.handle.net/21.11116/0000-0006-E9C6-4
Genre: Journal Article

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 Creators:
Pereira, Claney Lebev1, Author              
Geißner, Andreas2, Author              
Anish, Chakkumkal2, Author              
Seeberger, Peter H.1, Author              
Affiliations:
1Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863308              
2Chakkumal Anish, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863299              

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Free keywords: antigens, oligosaccharides, pyruvate acetal, Streptococcus pneumoniae, synthetic vaccines
 Abstract: Abstract Carbohydrate modifications are believed to strongly affect the immunogenicity of glycans. Capsular polysaccharides (CPS) from bacterial pathogens are frequently equipped with a pyruvate that can be placed across the 4,6-, 3,4-, or 2,3-positions. A trans-2,3-linked pyruvate is present on the CPS of the Gram-positive bacterium Streptococcus pneumoniae serotype 4 (ST4), a pathogen responsible for pneumococcal infections. To assess the immunological importance of this modification within the CPS repeating unit, the first total synthesis of the glycan was carried out. Glycan microarrays containing a series of synthetic antigens demonstrated how antibodies raised against natural ST4 CPS specifically recognize the pyruvate within the context of the tetrasaccharide repeating unit. The pyruvate modification is a key motif for designing minimal synthetic carbohydrate vaccines for ST4.

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Language(s): eng - English
 Dates: 2015-07-242015
 Publication Status: Published in print
 Pages: -
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 Table of Contents: -
 Rev. Type: -
 Identifiers: DOI: 10.1002/anie.201504847
BibTex Citekey: doi:10.1002/anie.201504847
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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 54 (34) Sequence Number: - Start / End Page: 10016 - 10019 Identifier: ISSN: 1433-7851