title: Determination of native capsular polysaccharide structures of Streptococcus pneumoniae serotypes 39, 42, and 47F and comparison to genetically or serologically related strains.
abstract: The diversity of capsular polysaccharides of the bacterial pathogen Streptococcus pneumoniae leads to at least 91 different serotypes. While the genetic loci for capsular biosynthesis have been characterized for all serotypes, the determination of resultant polysaccharide structures remains incomplete. Here, we report the chemical structures of the capsular polysaccharides of serotypes 39, 42, and 47F from the genetic cluster 4, and discuss the structures in the context of structures from serologically and genetically related serotypes. Antigenic determinants can be approximated in this manner. The structure of the serotype 39 capsular polysaccharide is [formula: see text] and has identical composition to the capsular polysaccharide 10A, but two different linkages. The serotype 42 structure [formula: see text] closely resembles the genetically related serotype 35A, which does not contain residue A. The structure of the serotype 47F capsular polysaccharide [formula: see text] is somewhat different from a recently determined structure from the same serogroup, while containing a structural motif that is reflected in serotype 35A and 42 capsular polysaccharide structures, thus explaining the cross-reactivity of serotype 47F with the typing serum 35a.
authors.affiliation: Carlsberg Laboratory, Gamle Carlsberg Vej 10, DK-1799 Copenhagen V, Denmark; Novo Nordisk A/S, Novo Nordisk Park, DK-2760 Måløv, Denmark. Electronic address: beop@novonordisk.com.
authors.forename: Bent O
authors.initials: BO
authors.lastname: Petersen
authors.affiliation: Carlsberg Laboratory, Gamle Carlsberg Vej 10, DK-1799 Copenhagen V, Denmark; Department of Chemistry, Technical University of Denmark, Kemitorvet, Building 201, DK-2800 Kgs. Lyngby, Denmark.
authors.forename: Sebastian
authors.initials: S
authors.lastname: Meier
authors.affiliation: Farmasøytisk institutt, Sem Sælands vei 3, N-0316 Oslo, Norway.
authors.forename: Berit Smestad
authors.initials: BS
authors.lastname: Paulsen
authors.affiliation: Statens Serum Institut, Artillerivej 5, DK-2300 Copenhagen S, Denmark.
authors.forename: Antonio R
authors.initials: AR
authors.lastname: Redondo
authors.affiliation: Statens Serum Institut, Artillerivej 5, DK-2300 Copenhagen S, Denmark.
authors.forename: Ian C
authors.initials: IC
authors.lastname: Skovsted
mesh_terms: D016667:Bacterial Capsules / Q000737:chemistry* / Q000276:immunology; D002240:Carbohydrate Sequence; D003429:Cross Reactions; D000939:Epitopes / Q000737:chemistry / Q000276:immunology; D016680:Genome, Bacterial; D006801:Humans; D007106:Immune Sera / Q000737:chemistry; D008969:Molecular Sequence Data; D005810:Multigene Family; D011135:Polysaccharides, Bacterial / Q000737:chemistry* / Q000276:immunology; D065288:Serogroup; D012703:Serotyping; D013296:Streptococcus pneumoniae / Q000737:chemistry* / Q000235:genetics / Q000276:immunology
chemical_list: D000939:Epitopes; D007106:Immune Sera; D011135:Polysaccharides, Bacterial
keywords: Capsular polysaccharide; NMR; Serotype 39; Serotype 42; Serotype 47F; Streptococcus pneumoniae