title: Chemical Synthesis Elucidates the Immunological Importance of a Pyruvate Modification in the Capsular Polysaccharide of Streptococcus pneumoniae Serotype 4.
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.
authors.affiliation: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14424 Potsdam (Germany) http://www.mpikg.mpg.de/en/bs. Claney.pereira@mpikg.mpg.de.|Institute of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin (Germany). Claney.pereira@mpikg.mpg.de.
authors.forename: Claney L
authors.initials: CL
authors.lastname: Pereira
authors.affiliation: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14424 Potsdam (Germany) http://www.mpikg.mpg.de/en/bs.|Institute of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin (Germany).
authors.forename: Andreas
authors.initials: A
authors.lastname: Geissner
authors.affiliation: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14424 Potsdam (Germany) http://www.mpikg.mpg.de/en/bs.|Institute of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin (Germany).
authors.forename: Chakkumkal
authors.initials: C
authors.lastname: Anish
authors.affiliation: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14424 Potsdam (Germany) http://www.mpikg.mpg.de/en/bs. Seeberger@mpikg.mpg.de.|Institute of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin (Germany). Seeberger@mpikg.mpg.de.
authors.forename: Peter H
authors.initials: PH
authors.lastname: Seeberger
mesh_terms: D011135:Polysaccharides, Bacterial / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology; D019289:Pyruvic Acid / Q000737:chemistry* / Q000276:immunology; D065288:Serogroup; D013296:Streptococcus pneumoniae / Q000737:chemistry* / Q000276:immunology
chemical_list: D011135:Polysaccharides, Bacterial; D019289:Pyruvic Acid
keywords: Streptococcus pneumoniae; antigens; oligosaccharides; pyruvate acetal; synthetic vaccines