Chemical Synthesis Elucidates the Immunological Importance of a Pyruvate Modification in the Capsular Polysaccharide of Streptococcus pneumoniae Serotype 4

作者: Claney L. Pereira , Andreas Geissner , Chakkumkal Anish , Peter H. Seeberger

DOI: 10.1002/ANIE.201504847

关键词:

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

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