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1. Compound ID: 189
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a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-+ a-L-Rhap-(1-3)-+
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a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-Glcp2Ac-(1-4)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-1)-D-Glc-ol |
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Structure type: oligomer
Contained glycoepitopes: IEDB_114708,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144825,IEDB_144826,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_192,SB_61,SB_7
The structure is contained in the following publication(s):
- Article ID: 43
Deng LY, Kasper DL, Krick TP, Wessels MR "Characterization of the linkage between the type III capsular polysaccharide and the bacterial cell wall of group B Streptococcus" -
Journal of Biological Chemistry 275(11) (2000) 7497-7504
The capsular polysaccharide of group B Streptococcus is a key virulence factor and an important target for protective immune responses. Until now, the nature of the attachment between the capsular polysaccharide and the bacterial cell has been poorly defined. We isolated insoluble cell wall fragments from lysates of type III group B Streptococcus and showed that the complexes contained both capsular polysaccharide and group B carbohydrate covalently bound to peptidoglycan. Treatment with the endo-N-acetylmuramidase mutanolysin released soluble complexes of capsular polysaccharide linked to group B carbohydrate by peptidoglycan fragments. Capsular polysaccharide could be enzymatically cleaved from group B carbohydrate by treatment of the soluble complexes with β-N-acetylglucosaminidase, which catalyzes hydrolysis of the β-D-GlcNAc(1→4)β-D-MurNAc subunit produced by mutanolysin digestion of peptidoglycan. Evidence from gas chromatography/mass spectrometry and (31)P NMR analysis of the separated polysaccharides supports a model of the group B Streptococcus cell surface in which the group B carbohydrate and the capsular polysaccharide are independently linked to the glycan backbone of cell wall peptidoglycan; group B carbohydrate is linked to N-acetylmuramic acid, and capsular polysaccharide is linked via a phosphodiester bond and an oligosaccharide linker to N-acetylglucosamine
polysaccharide, Streptococcus, capsular polysaccharide, type, group B Streptococcus, cell wall, linkage
NCBI PubMed ID: 10713053Publication DOI: 10.1074/jbc.275.11.7497Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: mwessels@channing.harvard.edu
Institutions: Channing Laboratory, Brigham and Women's Hospital, Harvard Medical School, Boston, Massachusetts 02115, USA
Methods: enzymatic degradation
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2. Compound ID: 190
|
a-L-Rhap-(1-2)-+ a-L-Rhap-(1-3)-+
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a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-a-L-Rhap-(1-2)-a-L-Rhap-(1-1)-D-Glc-ol |
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Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_114708,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_144825,IEDB_144826,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
The structure is contained in the following publication(s):
- Article ID: 43
Deng LY, Kasper DL, Krick TP, Wessels MR "Characterization of the linkage between the type III capsular polysaccharide and the bacterial cell wall of group B Streptococcus" -
Journal of Biological Chemistry 275(11) (2000) 7497-7504
The capsular polysaccharide of group B Streptococcus is a key virulence factor and an important target for protective immune responses. Until now, the nature of the attachment between the capsular polysaccharide and the bacterial cell has been poorly defined. We isolated insoluble cell wall fragments from lysates of type III group B Streptococcus and showed that the complexes contained both capsular polysaccharide and group B carbohydrate covalently bound to peptidoglycan. Treatment with the endo-N-acetylmuramidase mutanolysin released soluble complexes of capsular polysaccharide linked to group B carbohydrate by peptidoglycan fragments. Capsular polysaccharide could be enzymatically cleaved from group B carbohydrate by treatment of the soluble complexes with β-N-acetylglucosaminidase, which catalyzes hydrolysis of the β-D-GlcNAc(1→4)β-D-MurNAc subunit produced by mutanolysin digestion of peptidoglycan. Evidence from gas chromatography/mass spectrometry and (31)P NMR analysis of the separated polysaccharides supports a model of the group B Streptococcus cell surface in which the group B carbohydrate and the capsular polysaccharide are independently linked to the glycan backbone of cell wall peptidoglycan; group B carbohydrate is linked to N-acetylmuramic acid, and capsular polysaccharide is linked via a phosphodiester bond and an oligosaccharide linker to N-acetylglucosamine
polysaccharide, Streptococcus, capsular polysaccharide, type, group B Streptococcus, cell wall, linkage
NCBI PubMed ID: 10713053Publication DOI: 10.1074/jbc.275.11.7497Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: mwessels@channing.harvard.edu
Institutions: Channing Laboratory, Brigham and Women's Hospital, Harvard Medical School, Boston, Massachusetts 02115, USA
Methods: enzymatic degradation
- Article ID: 1752
Michon F, Katzenellenbogen E, Kasper DL, Jennings HJ "Structure of the complex group-specific polysaccharide of Group B Streptococcus" -
Biochemistry 26 (1987) 476-486
The group-specific antigen was isolated from a type Ia group B streptococcal strain and is a complex polysaccharide composed of α-L-rhamnopyranosyl, α-D-galactopyranosyl, 2-acetamido-2-deoxy-β-D-glucopyranosyl, D-glucitol, and phosphate residues. The complexity of the group B polysaccharide antigen is evident from the fact that when depolymerized by basic hydrolysis it yielded three structurally related, but nevertheless significantly different, oligosaccharides. These oligosaccharides were obtained in different molar quantities as their monophosphate esters. This evidence strongly suggests that they are linked by phosphodiester bonds in the original group B antigen. If these oligosaccharides are in fact randomly situated throughout the linear polysaccharide, then this type of heterogeneous repeating unit is unusual for a polysaccharide of bacterial origin. However, this structural arrangement of the oligosaccharides has yet to be unambiguously established because the alternate explanation of there being three different polysaccharides in the group B antigen cannot be discounted in the evidence presented here. The oligosaccharides were enzymatically dephosphorylated, and the structures of two of the three oligosaccharides are (formula: see text) Despite their structural differences, the two oligosaccharides are related by the smaller being an integral part of the larger. In the structural analysis of the group B antigen, methylation analysis, periodate oxidation, nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, fast atom bombardment mass spectrometry, and various specific chemical and enzymatic degradations were the principal methods used. Of particular interest was the use of an α-rhamnosidase to selectively degrade the larger oligosaccharide. This facilitated the assignment of signals in its 1H and 13C NMR spectra.
NCBI PubMed ID: 3548820Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A OR6
Methods: 13C NMR, 1H NMR
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3. Compound ID: 4562
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a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-+ a-L-Rhap-(1-3)-+
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a-L-Rhap-(1-3)-a-D-Galp-(1-3)-a-D-GlcpNAc-(1-4)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-1)-D-Glc-ol |
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Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_114708,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_144825,IEDB_144826,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
The structure is contained in the following publication(s):
- Article ID: 1755
Michon F, Brisson JR, Dell A, Kasper DL, Jennings HJ "Multiantennary group-specific polysaccharide of group B Streptococcus" -
Biochemistry 27 (1988) 5341-5351
The group-specific antigen of group B Streptococcus is composed of four different oligosaccharide units of Mw 766 (III), 1277 (II), 1462 (IV), and 1788 (I). The major constituent sugars of the oligosaccharides are α-L-rhamnopyranose, α-D-galactopyranose, 2-acetamido-2-deoxy-β-D-glucopyranosyl, and D-glucitol except that III does not contain α-D-galactopyranosyl or 2-acetamido-2-deoxy-β-D-glucopyranosyl residues and IV contains no D-glucitol but has one additional β-L-rhamnopyranosyl residue. The structures of II and III have been previously elucidated [Michon, F., Katzenellenbogen, E., Kasper, D. L., & Jennings, H. J. (1987) Biochemistry 26, 476-486]. In the group B antigen all the oligosaccharides are linked by one type of phosphodiester bond from O6 of the D-glucitol residue of one oligosaccharide to O6 of the α-D-galactopyranosyl residue of the next to form a complex and highly branched multiantennary structure. However, despite the heterogeneous nature of its component oligosaccharides, some order has been identified in the biosynthesis of the group B antigen from chemical and enzymatic sequence studies. Because III lacks an α-D-galactopyranosyl residue but has a D-glucitol residue, it is situated at the reducing terminus of all the branches of the group B antigen where it is always adjacent to a II moiety. Conversely, IV has an α-D-galactopyranosyl residue but has no D-glucitol and is therefore located at the reducing terminus of the group B antigen where it probably functions as a linker molecule between the group B polysaccharide and the cell wall peptidoglycan of the group B streptococcal organisms. Oligosaccharide I contains two α-D-galactopyranosyl residues and one D-glucitol residue and thus constitutes the branch point in the group B antigen, whereas II contains one of each of the above residues and therefore is situated in linear interchain positions. The group B antigen is highly branched and probably has a unique multiantennary structure.
NCBI PubMed ID: 3048399Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario
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4. Compound ID: 8088
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a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-+ a-L-Rhap-(1-3)-+
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a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-1)-D-Glc-ol-(6-P |
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Structure type: oligomer
Trivial name: oligosaccharide of GBC
Contained glycoepitopes: IEDB_114708,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_144825,IEDB_144826,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
The structure is contained in the following publication(s):
- Article ID: 3549
Sutcliffe IC, Black GW, Harrington DJ "Bioinformatic insights into the biosynthesis of the Group B carbohydrate in Streptococcus agalactiae" -
Microbiology (2008) 1354-1363
Streptococcus agalactiae is a major human and animal pathogen, most notable as a cause of life-threatening disease in neonates. S. agalactiae is also called the Group B Streptococcus in reference to the diagnostically significant Lancefield Group B typing antigen. Although the structure of this complex carbohydrate antigen has been solved, little is known of its biosynthesis beyond the identification of a relevant locus in sequenced S. agalactiae genomes. Analysis of the sugar linkages present in the Group B carbohydrate (GBC) structure has allowed us to deduce the minimum enzymology required to complete its biosynthesis. Most of the enzymes required to complete this biosynthesis can be identified within the putative biosynthetic locus. Surprisingly, however, three crucial N-acetylglucosamine transferases and enzymes required for activated precursor synthesis are not apparently located in this locus. A model for GBC biosynthesis wherein the complete polymer is assembled at the cytoplasmic face of the plasma membrane before translocation to the cell surface is proposed. These analyses also suggest that GBC is the major teichoic acid-like polymer in the cell wall of S. agalactiae, whereas lipoteichoic acid is the dominant poly(glycerophosphate) antigen. Genomic analysis has allowed us to predict the pathway leading to the biosynthesis of GBC of S. agalactiae
biosynthesis, structure, translocation, transferase, cell wall, Streptococcus agalactiae, typing, teichoic acid-like, Computational Biology
NCBI PubMed ID: 18451044Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: iain.sutcliffe@unn.ac.uk
Institutions: Northumbria University, Newcastle upon Tyne NE1 8ST, UK
Methods: genetic methods, biochemical methods
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5. Compound ID: 8089
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a-L-Rhap-(1-2)-+ a-L-Rhap-(1-3)-+
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a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-a-L-Rhap-(1-2)-a-L-Rhap-(1-1)-D-Glc-ol-(6-P |
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Structure type: oligomer
Trivial name: component the oligosaccharide of GBC
Contained glycoepitopes: IEDB_114708,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_144825,IEDB_144826,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
The structure is contained in the following publication(s):
- Article ID: 3549
Sutcliffe IC, Black GW, Harrington DJ "Bioinformatic insights into the biosynthesis of the Group B carbohydrate in Streptococcus agalactiae" -
Microbiology (2008) 1354-1363
Streptococcus agalactiae is a major human and animal pathogen, most notable as a cause of life-threatening disease in neonates. S. agalactiae is also called the Group B Streptococcus in reference to the diagnostically significant Lancefield Group B typing antigen. Although the structure of this complex carbohydrate antigen has been solved, little is known of its biosynthesis beyond the identification of a relevant locus in sequenced S. agalactiae genomes. Analysis of the sugar linkages present in the Group B carbohydrate (GBC) structure has allowed us to deduce the minimum enzymology required to complete its biosynthesis. Most of the enzymes required to complete this biosynthesis can be identified within the putative biosynthetic locus. Surprisingly, however, three crucial N-acetylglucosamine transferases and enzymes required for activated precursor synthesis are not apparently located in this locus. A model for GBC biosynthesis wherein the complete polymer is assembled at the cytoplasmic face of the plasma membrane before translocation to the cell surface is proposed. These analyses also suggest that GBC is the major teichoic acid-like polymer in the cell wall of S. agalactiae, whereas lipoteichoic acid is the dominant poly(glycerophosphate) antigen. Genomic analysis has allowed us to predict the pathway leading to the biosynthesis of GBC of S. agalactiae
biosynthesis, structure, translocation, transferase, cell wall, Streptococcus agalactiae, typing, teichoic acid-like, Computational Biology
NCBI PubMed ID: 18451044Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: iain.sutcliffe@unn.ac.uk
Institutions: Northumbria University, Newcastle upon Tyne NE1 8ST, UK
Methods: genetic methods, biochemical methods
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6. Compound ID: 13881
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a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-a-L-Rhap-(1-2)-{{{-a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-}}}a-L-Rhap-(1-2)-a-L-Rhap-(1-1)-D-Glc-ol-(3-1)-a-L-Rhap |
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Structure type: fragment of a bigger structure
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_114708,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_144826,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
The structure is contained in the following publication(s):
- Article ID: 5485
Paoletti LC, Kasper DL "Surface Structures of Group B Streptococcus Important in Human Immunity" -
Microbiology Spectrum 7(2) (2019) ID GPP3-0001-2017
The surface of the Gram-positive opportunistic pathogen Streptococcus agalactiae, or group B Streptococcus (GBS), harbors several carbohydrate and protein antigens with the potential to be effective vaccines. Capsular polysaccharides of all clinically-relevant GBS serotypes coupled to immunogenic proteins of both GBS and non-GBS origin have undergone extensive testing in animals that led to advanced clinical trials in healthy adult women. In addition, GBS proteins either alone or in combination have been tested in animals; a fusion protein construct has recently advanced to human clinical studies. Given our current understanding of the antigenicity and immunogenicity of the wide array of GBS surface antigens, formulations now exist for the generation of viable vaccines against diseases caused by GBS.
structure, capsular polysaccharides, group B Streptococcus, surface, vaccines, Streptococcus agalactiae, Gram-positive
NCBI PubMed ID: 30873933Publication DOI: 10.1128/microbiolspec.GPP3-0001-2017Journal NLM ID: 101634614Publisher: Washington, DC: ASM Press
Correspondence: Lawrence C. Paoletti
Institutions: Division of Immunology, Department of Microbiology and Immunobiology, Harvard Medical School, Boston, MA 02115
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7. Compound ID: 13882
|
a-L-Rhap-(1-2)-{{{-a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-}}}a-L-Rhap-(1-2)-a-L-Rhap-(1-1)-D-Glc-ol-(3-1)-a-L-Rhap |
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Structure type: fragment of a bigger structure
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_114708,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_144826,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
The structure is contained in the following publication(s):
- Article ID: 5485
Paoletti LC, Kasper DL "Surface Structures of Group B Streptococcus Important in Human Immunity" -
Microbiology Spectrum 7(2) (2019) ID GPP3-0001-2017
The surface of the Gram-positive opportunistic pathogen Streptococcus agalactiae, or group B Streptococcus (GBS), harbors several carbohydrate and protein antigens with the potential to be effective vaccines. Capsular polysaccharides of all clinically-relevant GBS serotypes coupled to immunogenic proteins of both GBS and non-GBS origin have undergone extensive testing in animals that led to advanced clinical trials in healthy adult women. In addition, GBS proteins either alone or in combination have been tested in animals; a fusion protein construct has recently advanced to human clinical studies. Given our current understanding of the antigenicity and immunogenicity of the wide array of GBS surface antigens, formulations now exist for the generation of viable vaccines against diseases caused by GBS.
structure, capsular polysaccharides, group B Streptococcus, surface, vaccines, Streptococcus agalactiae, Gram-positive
NCBI PubMed ID: 30873933Publication DOI: 10.1128/microbiolspec.GPP3-0001-2017Journal NLM ID: 101634614Publisher: Washington, DC: ASM Press
Correspondence: Lawrence C. Paoletti
Institutions: Division of Immunology, Department of Microbiology and Immunobiology, Harvard Medical School, Boston, MA 02115
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8. Compound ID: 16329
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a-L-Rhap-(1-2)-+ a-L-Rhap-(1-3)-+
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a-L-Rhap-(1-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-a-L-Rhap-(1-2)-a-L-Rhap-(1-1)-D-Glc-ol-(6---P---/(CH2)6NH2, CRM(197)/ |
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Structure type: oligomer
; 1457.5803 [M+Na]+
C56H101N2O39P
Aglycon: (CH2)6NH2, CRM(197)
Trivial name: GBC subunit II
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_114708,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_144825,IEDB_144826,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
The structure is contained in the following publication(s):
- Article ID: 6335
Wang Z, Enotarpi J, Buff G, Pezzicoli A, Gstöttner CJ, Nicolardi S, Balducci E, Fabbrini M, Romano MR, van der Marel GA, Del Bino L, Adamo R, Codee JDC "Chemical Synthesis and Immunological Evaluation of Fragments of the Multiantennary Group-Specific Polysaccharide of Group B Streptococcus" -
Journal of the American Chemical Society Au 2(7) (2022) 1724-1735
Group B Streptococcus (GBS) is a Gram-positive bacterium and the most common cause of neonatal blood and brain infections. At least 10 different serotypes exist, that are characterized by their different capsular polysaccharides. The Group B carbohydrate (GBC) is shared by all serotypes and therefore attractive be used in a glycoconjugate vaccine. The GBC is a highly complex multiantennary structure, composed of rhamnose rich oligosaccharides interspaced with glucitol phosphates. We here report the development of a convergent approach to assemble a pentamer, octamer, and tridecamer fragment of the termini of the antennae. Phosphoramidite chemistry was used to fuse the pentamer and octamer fragments to deliver the 13-mer GBC oligosaccharide. Nuclear magnetic resonance spectroscopy of the generated fragments confirmed the structures of the naturally occurring polysaccharide. The fragments were used to generate model glycoconjugate vaccine by coupling with CRM197. Immunization of mice delivered sera that was shown to be capable of recognizing different GBS strains. The antibodies raised using the 13-mer conjugate were shown to recognize the bacteria best and the serum raised against this GBC fragment-mediated opsonophagocytic killing best, but in a capsule dependent manner. Overall, the GBC 13-mer was identified to be a highly promising antigen for incorporation into future (multicomponent) anti-GBS vaccines.
synthesis, capsular polysaccharide, Oligosaccharides, group B Streptococcus, glycoconjugate vaccine
NCBI PubMed ID: 35911445Publication DOI: 10.1021/jacsau.2c00302Journal NLM ID: 101775714Publisher: Washington, DC: American Chemical Society
Correspondence: J.D.C. Codée
Institutions: Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands, Center for Proteomics and Metabolomics, Leiden University Medical Center, Albinusdreef 2, 2333 ZA Leiden, The Netherlands, GSK Siena Italy, Via Fiorentina 1 Siena 53100, Italy
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, ELISA, 31P NMR, chemical synthesis, UV, glycosylation, microscopy, optical rotation measurement, HPTLC, column chromatography, immunization, conjugation, HR-ESI-MS
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9. Compound ID: 16330
|
a-L-Rhap-(1-3)-+ a-L-Rhap-(1-3)-+ a-L-Rhap-(1-2)-+ a-L-Rhap-(1-3)-+
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a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-1)-D-Glc-ol-(6--P--6)--a-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-a-L-Rhap-(1-2)-a-L-Rhap-(1-1)-D-Glc-ol-(6---P---/(CH2)6NH2, CRM(197)/ |
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Structure type: oligomer
; 2285.8435 [M+Na]+
C86H154N2O63P2
Aglycon: (CH2)6NH2, CRM(197)
Trivial name: GBC subunit III + sub II
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_114708,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_144825,IEDB_144826,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
The structure is contained in the following publication(s):
- Article ID: 6335
Wang Z, Enotarpi J, Buff G, Pezzicoli A, Gstöttner CJ, Nicolardi S, Balducci E, Fabbrini M, Romano MR, van der Marel GA, Del Bino L, Adamo R, Codee JDC "Chemical Synthesis and Immunological Evaluation of Fragments of the Multiantennary Group-Specific Polysaccharide of Group B Streptococcus" -
Journal of the American Chemical Society Au 2(7) (2022) 1724-1735
Group B Streptococcus (GBS) is a Gram-positive bacterium and the most common cause of neonatal blood and brain infections. At least 10 different serotypes exist, that are characterized by their different capsular polysaccharides. The Group B carbohydrate (GBC) is shared by all serotypes and therefore attractive be used in a glycoconjugate vaccine. The GBC is a highly complex multiantennary structure, composed of rhamnose rich oligosaccharides interspaced with glucitol phosphates. We here report the development of a convergent approach to assemble a pentamer, octamer, and tridecamer fragment of the termini of the antennae. Phosphoramidite chemistry was used to fuse the pentamer and octamer fragments to deliver the 13-mer GBC oligosaccharide. Nuclear magnetic resonance spectroscopy of the generated fragments confirmed the structures of the naturally occurring polysaccharide. The fragments were used to generate model glycoconjugate vaccine by coupling with CRM197. Immunization of mice delivered sera that was shown to be capable of recognizing different GBS strains. The antibodies raised using the 13-mer conjugate were shown to recognize the bacteria best and the serum raised against this GBC fragment-mediated opsonophagocytic killing best, but in a capsule dependent manner. Overall, the GBC 13-mer was identified to be a highly promising antigen for incorporation into future (multicomponent) anti-GBS vaccines.
synthesis, capsular polysaccharide, Oligosaccharides, group B Streptococcus, glycoconjugate vaccine
NCBI PubMed ID: 35911445Publication DOI: 10.1021/jacsau.2c00302Journal NLM ID: 101775714Publisher: Washington, DC: American Chemical Society
Correspondence: J.D.C. Codée
Institutions: Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands, Center for Proteomics and Metabolomics, Leiden University Medical Center, Albinusdreef 2, 2333 ZA Leiden, The Netherlands, GSK Siena Italy, Via Fiorentina 1 Siena 53100, Italy
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, ELISA, 31P NMR, chemical synthesis, UV, glycosylation, microscopy, optical rotation measurement, HPTLC, column chromatography, immunization, conjugation, HR-ESI-MS
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Total list of corresponding CSDB IDs (record IDs):
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