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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_146668,IEDB_146669,IEDB_146671,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

• Article ID: 312
  Lucas AH, Granoff DM, Mandrell RE, Connolly CC, Shan AS, Powers DC "Oligoclonality of serum immunoglobulin G antibody responses to Streptococcus pneumoniae capsular polysaccharide serotypes 6B, 14, and 23F" - Infection and Immunity 65(12) (1997) 5103-5109
  

  Serum antibodies (Abs) specific for the capsular polysaccharides of Streptococcus pneumoniae provide protection against invasive pneumococcal disease. Previous studies indicate that Abs to pneumococcal polysaccharide (PPS) serotypes 1 and 6B have limited clonal diversity. To determine if restricted diversity was a feature common to other PPS specificities, we examined the light (L)-chain expression and isoelectric heterogeneity of type 6B, 14, and 23F Abs elicited in 15 adults following PPS vaccination. At the population level, both PPS-6B and PPS-14 Abs expressed kappa and lambda chains, although 6B Abs more frequently expressed lambda chains lambda and 14 Abs more frequently expressed kappa chains. In individual sera, Abs were generally skewed towards either kappa or lambda expression. 23F-specific Abs had predominantly kappa chains. Isoelectric focusing analyses showed that sera contained one or at most a few immunoglobulin G Ab spectrotypes to all three respective capsular serotypes, a result indicative of oligoclonality. A sequence analysis of a purified PPS-14-specific Ab having a single spectrotype gave uniform amino-terminal sequences for both the heavy chain (V(H)III subgroup) and the L chain (kappaIII-A27 V region). From these results we conclude that within individual adults, serum Ab responses to PPS serotypes 6B, 14, and 23F derive from a small number of dominant B-cell clones, and consequently variable-region expression is probably individually limited as well. Oligoclonality appears to be a general characteristic of human PPS-specific Ab repertoires, and we suggest that this property could lead to individual differences in Ab fine specificity and/or functional activity against encapsulated pneumococci.

  serotype, Streptococcus, Streptococcus pneumoniae, capsular polysaccharide, antibody response, immunoglobulins

  NCBI PubMed ID: 9393802
  Journal NLM ID: 0246127
  Publisher: American Society for Microbiology
  Institutions: Children's Hospital Oakland Research Institute, Oakland, California 94609, Chiron Vaccines, Emeryville, California, 94608, Departament of Internal Medicine and The Center for Vaccine Development, St. Louis, Missouri 63110.
  Methods: serological methods
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 7503 (all data & tools)
• Article ID: 506
  Pujar NS, Huang NF, Daniels CL, Dieter L, Gayton MG, Lee AL "Base hydrolysis of phosphodiester bonds in pneumococcal polysaccharides" - Biopolymers 75(1) (2004) 71-84
  

  A comprehensive study of the base hydrolysis of all phosphodiester bond-containing capsular polysaccharides of the 23-valent pneumococcal vaccine is described here. Capsular polysaccharides from serotypes 6B, 10A, 17F, 19A, 19F, and 20 contain a phosphodiester bond that connects the repeating units in these polysaccharides (also referred to as backbone phosphodiester bonds), and polysaccharides from serotypes 11A, 15B, 18C, and 23F contain a phosphodiester bond that links a side chain to their repeating units. Molecular weight measurements of the polysaccharides, using high performance size exclusion chromatography with tandem multiangle laser light scattering and refractive index detection, was used to evaluate the kinetics of hydrolysis. The measurement of molecular weight provides a high degree of sensitivity in the case of small extents of reaction, thus allowing reliable measurements of the kinetics over short times. Pseudo-first-order rate constants for these polysaccharides were estimated using a simple model that accounts for the polydispersity of the starting sample. It was found that the relative order of backbone phosphodiester bond instability due to base hydrolysis was 19A > 10A > 19F > 6B > 17F, 20. Degradation of side-chain phosphodiester bonds was not observed, although the high degree of sensitivity in measurements is lost in this case, due to the low contribution of the side chains to the total polysaccharide molecular weight. In comparison with literature data on pneumococcal polysaccharide 6A, 19A was found to be the more labile, and hence appears to be the most labile pneumococcal polysaccharide studied to date. The rate of hydrolysis increased at higher pH and in the presence of divalent cation, but the extent was lower than expected based on similar data on RNA. Finally, the differences in the phosphodiester bond stabilities were analyzed by considering stereochemical factors in these polysaccharides. These results also provide a framework for evaluation of molecular integrity of phosphodiester-bond-containing polysaccharides in different solution conditions. Copyright 2004 Wiley Periodicals, Inc. Biopolymers, 2004

  base hydrolysis, phosphodiester bond, pneumococcal polysaccharide

  NCBI PubMed ID: 15307199
  Journal NLM ID: 0372525
  Publisher: Wiley Interscience
  Correspondence: hari_pujar@merck.com
  Institutions: Merck Research Laboratories, Merck & Co., West Point, PA 19486
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 9352 (all data & tools)
• Article ID: 557
  Reason DC, Zhou J "Correlation of antigenic epitope and antibody gene usage in the human immune response to Streptococcus pneumoniae type 23F capsular polysaccharide" - Clinical Immunology 111(1) (2004) 132-136
  

  The human antibody response to the capsular polysaccharide of Streptococcus pneumoniae type 23F is predominated by antibodies which express either VkappaL6 or VkappaA23 light chain genes. In this report, we demonstrate that the antigenic epitopes recognized by these two families can be differentiated based on their specificity for the hapten l-rhamnose, a constituent sugar of the bacterial capsule polymer. The VkappaL6 family utilizes light chains with an unusually long third complementarity-determining region. These VkappaL6-encoded Fabs are 100-fold more sensitive to inhibition with l-rhamnose than VkappaA23 Fabs. VkappaL6 Fabs preferentially recognize the l-isomer of the hapten and can distinguish l-rhamnose from the structurally similar sugar l-mannose. We also demonstrate that the VkappaL6 family component of the antibody response recognizes the polysaccharide antigens of Group B streptococci (GBS), thereby accounting for the previously reported cross-reaction between PPS 23F-specific antisera and Group B streptococci

  Streptococcus pneumoniae, capsular polysaccharide, antigenic epitopes, Antibody repertoire

  NCBI PubMed ID: 15093562
  Journal NLM ID: 8804032
  Publisher: Toronto; Philadelphia: Decker; Saint Louis, MO: Sales and distribution, U.S. and Possessions, Mosby
  Correspondence: dreason@chori.org
  Institutions: Research Institute, Children's Hospital Oakland, Oakland, CA 94609, USA
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 9293 (all data & tools)
• Article ID: 1306
  Zamze S, Martinez-Pomares L, Jones H, Taylor PR, Stillion RJ, Gordon S, Wong SY "Recognition of bacterial capsular polysaccharides and lipopolysaccharides by the macrophage mannose receptor" - Journal of Biological Chemistry 277(44) (2002) 41613-41623
  

  The in vitro binding of the macrophage mannose receptor to a range of different bacterial polysaccharides was investigated. The receptor was shown to bind to purified capsular polysaccharides from Streptococcus pneumoniae and to the lipopolysaccharides, but not capsular polysaccharides, from Klebsiella pneumoniae. Binding was Ca(2+)- dependent and inhibitable with d-mannose. A fusion protein of the mannose receptor containing carbohydrate recognition domains 4-7 and a full-length soluble form of the mannose receptor containing all domains external to the transmembrane region both displayed very similar binding specificities toward bacterial polysaccharides, suggesting that domains 4-7 are sufficient for recognition of these structures. Surprisingly, no direct correlation could be made between polysaccharide structure and binding to the mannose receptor, suggesting that polysaccharide conformation may play an important role in recognition. The full-length soluble form of the mannose receptor was able to bind simultaneously both polysaccharide via the carbohydrate recognition domains and sulfated oligosaccharide via the cysteine-rich domain. The possible involvement of the mannose receptor, either cell surface or soluble, in the innate and adaptive immune responses to bacterial polysaccharides is discussed

  Lipopolysaccharide, conformation, lipopolysaccharides, oligosaccharide, structure, correlation, Bacterial, role, capsular, polysaccharide, Streptococcus, Streptococcus pneumoniae, D-mannose, capsular polysaccharide, capsular polysaccharides, polysaccharides, carbohydrate, cell, Research, form, recognition, involvement, protein, response, specificity, Klebsiella, Bacterial polysaccharide, region, external, surface, polysaccharide structure, purified, Klebsiella pneumoniae, bacterial polysaccharides, binding, domain, domains, vaccine, immune response, Mannose, immune, in vitro, macrophage, soluble, receptor, sulfated, pathology, carbohydrate recognition, carbohydrate recognition domain, fusion, fusion protein, transmembrane

  NCBI PubMed ID: 12196537
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: susanne.zamze@jenner.ac.uk
  Institutions: Edward Jenner Institute for Vaccine Research, Compton, Berkshire RG20 7NN, United Kingdom and the Sir William Dunn School of Pathology, University of Oxford, South Parks Road, Oxford OX1 3RE, United Kingdom
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 6071 (all data & tools)
• Article ID: 1346
  Abeygunawardana C, Williams TC, Sumner JS, Hennessey JP "Development and validation of an NMR-based identity assay for bacterial polysaccharides" - Analytical Biochemistry 279(2) (2000) 226-240
  

  A method utilizing NMR spectroscopy has been developed to confirm the identity of bacterial polysaccharides used to formulate a polyvalent pneumococcal polysaccharide vaccine. The method is based on 600 MHz proton NMR spectra of individual serotype-specific polysaccharides. A portion of the anomeric region of each spectrum (5.89 to 4.64 ppm) is compared to spectra generated for designated reference samples for each polysaccharide of interest. The selected region offers a spectral window that is unique to a given polysaccharide and is sensitive to any structural alteration of the repeating units. The similarity of any two spectral profiles is evaluated using a correlation coefficient (rho), where rho >/= 0.95 between a sample and reference profile indicates a positive identification of the sample polysaccharide. This method has been shown to be extremely selective in its ability to discriminate between serotype-specific polysaccharides, some of which differ by no more than a single glycosidic linkage. Furthermore, the method is rapid and does not require extensive sample manipulations or pretreatments. The method was validated as a qualitative identity assay and will be incorporated into routine quality control testing of polysaccharide powders to be used in preparation of the polyvalent pneumococcal vaccine PNEUMOVAX 23. The specificity and reproducibility of the NMR-based identity assay is superior to the currently used colorimetric assays and can be readily adapted for use with other bacterial polysaccharide preparations as well.

  NMR, Bacterial, polysaccharide, polysaccharides, Bacterial polysaccharide, bacterial polysaccharides, assay, development, identity assay, method development, validation

  NCBI PubMed ID: 10706792
  Publication DOI: 10.1006/abio.1999.447
  Journal NLM ID: 0370535
  Publisher: Academic Press
  Correspondence: abey@merck.com
  Institutions: Bioprocess and Bioanalytical Research, Merck Research Laboratories, West Point, Pensylvania, USA
  Methods: NMR
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 6414 (all data & tools)
• Article ID: 1519
  Jones C "NMR assays for carbohydrate-based vaccines" - Journal of Pharmaceutical and Biomedical Analysis 38(5) (2005) 840-850
  

  Antibodies against the cell surface carbohydrates of many microbial pathogens protect against infection. This was initially exploited by the development of purified polysaccharide vaccines, but glycoconjugate vaccines, in which the cell surface carbohydrate of a microbial pathogen is covalently attached to an appropriate carrier protein, are proving the most effective means to generate this protective immunity. Carbohydrate-based vaccines against Haemophilus influenzae Type b, Neisseria meningitidis, Streptococcus pneumoniae and Salmonella enterica serotype Typhi (S. Typhi) are already licensed, and many similar products are in various stages of development. For many of these vaccines, biological assays are not available or are inappropriate and NMR spectroscopy is proving a valuable tool for the characterisation and quality control of existing and novel products. This review highlights some of the areas in which NMR spectroscopy is currently used, and where further developments may be expected.

  capsular polysaccharide, O-acetylation, pneumonia, glycoconjugate, meningitis, carbohydrate-based vaccines, identity, typhoid

  NCBI PubMed ID: 16087046
  Publication DOI: 10.1016/j.jpba.2005.01.044
  Journal NLM ID: 8309336
  Publisher: London: Elsevier
  Institutions: Laboratory for Molecular Structure, National Institute for Biological Standards and Control, South Mimms, UK
  Methods: NMR
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 10377 (all data & tools)
• Article ID: 1715
  Richards JC, Perry MB "Structure of the specific capsular polysaccharide of Streptococcus pneumoniae type 23F (American type 23)" - Biochemistry and Cell Biology 66 (1988) 758-771
  

  The specific capsular polysaccharide of Streptococcus pneumoniae serotype 23F (American type 23) is composed of a repeating tetrasaccharide unit containing D-glucose (one part), D-galactose (one part), L-rhamnose (two parts), glycerol (one part), and phosphate (one part). By composition analysis, optical rotation, partial hydrolysis, periodate oxidation, methylation, and high-resolution 1H and 13C nuclear magnetic resonance studies, the elucidated unambiguous structure was in agreement with our earlier proposal but is at variance with structures proposed later by other authors. The structure of the type 23F pneumococcal polysaccharide is (formula; see text).

  NCBI PubMed ID: 2846013
  Journal NLM ID: 8606068
  Publisher: Ottawa: National Research Council of Canada
  Institutions: Division of Biological Sciences, National Research Council, Ottawa, Ont., Canada
  Methods: 13C NMR, 1H NMR
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 105798 (all data & tools)
• Article ID: 2250
  Bednar B, Hennessey JP (JR) "Molecular size analysis of capsular polysaccharide preparations from Streptococcus pneumoniae" - Carbohydrate Research 243 (1993) 115-130
  

  Purified capsular polysaccharide preparations from Streptococcus pneumoniae serotypes 4, 6B, 9V, 14, 18C, 19F, and 23F were analyzed by high performance size exclusion chromatography (HPSEC) with multi-angle laser light scattering (MALLS), specific viscosity (SV), and refractive index (RI) detection to determine the molecular size and molar mass of each of the pneumococcal (Pn) polysaccharides. The Mw's of the polysaccharides ranged from a low of 606 kg/mol for Pn4 to a high of 1145 kg/mol for Pn9V, and the z-average radii of gyration ranged from 59 nm for Pn14 to 72 nm for Pn18C. Estimations of molar mass of the highly anionic polysaccharides (all but Pn14) by the universal calibration approach were unsuccessful, resulting in a 27-53% overestimate of the Mw's though application of Mark-Houwink-Sakurada coefficients calculated from the HPSEC-MALLS/SV/RI data resulted in estimates of Mw that were in agreement with the MALLS estimates for all but the Pn4 preparation. These results emphasize the need for direct measurement of both molecular size and intrinsic viscosity distributions for definitive characterization of the molar mass, hydrodynamic volume, rigidity, and drainage of complex biological polymers such as the pneumococcal polysaccharides.

  NCBI PubMed ID: 8324758
  Publication DOI: 10.1016/0008-6215(93)84085-k
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Department of Biological Chemistry, Merck Research Laboratories, West Point, Pennsylvania
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 117211 (all data & tools)
• Article ID: 2514
  Arndt B, Porro M "Strategies for type-specific glycoconjugate vaccines of Streptococcus pneumoniae" - Advances in Experimental Medicine and Biology 303 (1991) 129-148
  
  Journal NLM ID: 0121103
  Publisher: Kluwer Academic/Plenum Publishers
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 129932 (all data & tools)
• Article ID: 2805
  van Steijn AMP, Jetten M, Kamerling JP, Vliegenthart JFG "Synthesis of tri- and tetrasaccharide fragments of the capsular polysaccharide of Streptococcus pneumoniae type 23F" - Receuil des Travaux Chimiques des Pays-Bas [French] 108 (1989) 374-383
  
  Journal NLM ID: 9892037
  Publisher: Leide, Netherlands: A.W. Sijthoff
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 148197 (all data & tools)
• Article ID: 3839
  Dasgupta S, Nitz M "Synthesis of a core disaccharide from the Streptococcus pneumoniae type 23F capsular polysaccharide antigen" - Carbohydrate Research 345(15) (2010) 2282-2286
  

  The synthesis of methyl α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranoside and methyl α-L-rhamnopyranosyl-(1→2)-3-(glycer-2-yl-phosphate)-β-D-galactopy ranoside disaccharides from the Streptococcuspneumoniae type 23F capsular polysaccharide is reported. A simple protecting group strategy was followed using commercially available monosaccharides and phosphorylating reagents. H-Phosphonate and phosphoramidite coupling chemistries were explored for introducing the phosphodiester. Hydrazine hydrate was found to be a mild and efficient deacetylating agent, which was required to avoid phosphate migration during the deprotection of the phosphodiester functionalized disaccharide.

  Streptococcus pneumoniae, H-phosphonate, phosphoramidite, Phosphoglycan

  NCBI PubMed ID: 20810102
  Publication DOI: 10.1016/j.carres.2010.08.002
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: M. Nitz
  Institutions: Department of Chemistry, 80 St. George Str. Toronto, ON, Canada
  Methods: NMR, chemical synthesis
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 25225 (all data & tools)
• Article ID: 4430
  Ovodov YS "Bacterial capsular antigens. Structural patterns of capsular antigens" - Biochemistry (Moscow) 71(9) (2006) 937-954
  

  Structural patterns of bacterial capsular antigens including capsular polysaccharides and exoglycans are given in this review. In addition, the immunological activity of capsular antigens and their role in type specificity of bacteria are discussed.

  structure, capsular polysaccharides, bacterial capsular antigens, bacterial exoglycans, immunological activity, type specificity

  NCBI PubMed ID: 17009947
  Publication DOI: 10.1134/S000629790609001X
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Correspondence: ovoys@physiol.komisc.ru
  Institutions: Institute of Physiology, Komi Science Center, Urals Branch of the Russian Academy of Sciences, Syktyvkar 167982, Russia
  
   
  
  Streptococcus pneumoniae type 23F
  CSDB ID 28718 (all data & tools)
• Article ID: 4827
  Geno KA, Gilbert GL, Song JY, Skovsted IC, Klugman KP, Jones C, Konradsen HB, Nahm MH "Pneumococcal Capsules and Their Types: Past, Present, and Future" - Clinical Microbiology Reviews 28(3) (2015) 871-899
  

  Streptococcus pneumoniae (the pneumococcus) is an important human pathogen. Its virulence is largely due to its polysaccharide capsule, which shields it from the host immune system, and because of this, the capsule has been extensively studied. Studies of the capsule led to the identification of DNA as the genetic material, identification of many different capsular serotypes, and identification of the serotype-specific nature of protection by adaptive immunity. Recent studies have led to the determination of capsular polysaccharide structures for many serotypes using advanced analytical technologies, complete elucidation of genetic basis for the capsular types, and the development of highly effective pneumococcal conjugate vaccines. Conjugate vaccine use has altered the serotype distribution by either serotype replacement or switching, and this has increased the need to serotype pneumococci. Due to great advances in molecular technologies and our understanding of the pneumococcal genome, molecular approaches have become powerful tools to predict pneumococcal serotypes. In addition, more-precise and -efficient serotyping methods that directly detect polysaccharide structures are emerging. These improvements in our capabilities will greatly enhance future investigations of pneumococcal epidemiology and diseases and the biology of colonization and innate immunity to pneumococcal capsules.

  serotype, Streptococcus pneumoniae, vaccines, Pneumococcal Capsules

  NCBI PubMed ID: 26085553
  Publication DOI: 10.1128/CMR.00024-15
  Journal NLM ID: 8807282
  Publisher: Washington, DC: American Society for Microbiology
  Correspondence: Moon H. Nahm
  Institutions: Department of Pathology, University of Alabama at Birmingham, Birmingham, Alabama, USA, Centre for Infectious Diseases and Microbiology, Institute of Clinical Pathology & Medical Research, Westmead Hospital, Wentworthville, New South Wales, Australia, Marie Bashir Institute for Infectious Diseases and Biosecurity, University of Sydney, Sydney, New South Wales, Australia, Division of Infectious Disease, Department of Internal Medicine, Korea University Guro Hospital, Seoul, South Korea, SSI Diagnostica, Division of Microbiology and Diagnostics, Statens Serum Institut, Copenhagen, Denmark, Pneumonia Program Strategy Team, Bill & Melinda Gates Foundation, Seattle, Washington, USA, Laboratory for Molecular Structure, NIBSC, South Mimms, Herts, United Kingdom, Department of Microbiology, University of Alabama at Birmingham, Birmingham, Alabama, USA
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 31052 (all data & tools)
• Article ID: 4835
  Berti F, Ravenscroft N "Characterization of Carbohydrate Vaccines by NMR Spectroscopy" - Methods in Molecular Biology 1331 (2015) 189-209
  

  Physicochemical techniques are a powerful tool for the structural characterization of carbohydrate-based vaccines. High-field Nuclear Magnetic Resonance (NMR) spectroscopy has been established as an extremely useful and robust method for tracking the industrial manufacturing process of these vaccines from polysaccharide bulk antigen through to the final formulation. Here, we describe the use of proton NMR for structural identity and conformity testing of carbohydrate-based vaccines.

  carbohydrates, capsular polysaccharide, antigens, nuclear magnetic resonance spectroscopy, vaccines

  NCBI PubMed ID: 26169742
  Publication DOI: 10.1007/978-1-4939-2874-3_12
  Journal NLM ID: 9214969
  Publisher: Springer
  Correspondence: francesco.x.berti@gsk.com
  Institutions: Research, GSK Vaccines, Via Fiorentina 1, 53100, Siena, Italy
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 11115 (all data & tools)
• Article ID: 5036
  Ravenscroft N, Omar A, Hlozek J, Edmonds-Smith C, Follador R, Serventi F, Lipowsky G, Kuttel MM, Cescutti P, Faridmoayer A "Genetic and structural elucidation of capsular polysaccharides from Streptococcus pneumoniae serotype 23A and 23B, and comparison to serotype 23F" - Carbohydrate Research 450 (2017) 19-29
  

  Streptococcus pneumoniae is a globally important encapsulated human pathogen with approximately 100 different serotypes recognized. Serogroup 23 consists of serotype 23F, present in licensed vaccines, and emerging serotypes 23A and 23B. Here, we report the previously unknown structures of the pneumococcal capsular polysaccharides serotype 23A and 23B determined using genetic analysis, NMR spectroscopy, composition and linkage analysis and Smith degradation (of polysaccharide 23A). The structure of the serotype 23A capsular polysaccharide is: →4)-β-D-Glcp-(1→3)-[[α-L-Rhap-(1→2)]-[Gro-(2→P→3)]-β-D-Galp-( 1→4)]-β-L-Rhap-(1→. This structure differs from polysaccharide 23F as it features a disaccharide backbone and the di-substituted β-Gal is linked to β-Rha as a side chain. This is due to the different polymerization position catalysed by the unusually divergent repeat unit polymerase Wzy in the 23A cps biosynthesis locus. Steric crowding in 23A, confirmed by molecular models, causes the NMR signal for H-1 of the di-substituted 2,3-β-Gal to resonate in the α-anomeric region. The structure of the serotype 23B capsular polysaccharide is the same as 23F, but without the terminal α-Rha: →4)-β-D-Glcp-(1→4)-[Gro-(2→P→3)]-β-D-Galp-(1→4)-β-L-Rhap-(1→ . The immunodominant terminal α-Rha of 23F is more sterically crowded in 23A and absent in 23B. This may explain the reported typing cross reactions for serotype 23F: slight with 23A and none with 23B.

  Streptococcus pneumoniae, capsular polysaccharide, NMR spectroscopy, Serotype 23A, Serotype 23B

  NCBI PubMed ID: 28837839
  Publication DOI: 10.1016/j.carres.2017.08.006
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: neil.ravenscroft@uct.ac.za
  Institutions: Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa, Department of Computer Science, University of Cape Town, Rondebosch 7701, South Africa, Department of Life Sciences, Blg. C11, Universita di Trieste, via L. Giorgieri 1, 34127 Trieste, Italy, LimmaTech Biologics AG, Grabenstrasse 3, Schlieren, Switzerland
  Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, SDS-PAGE, sugar analysis, 31P NMR, acid hydrolysis, GC, Smith degradation, methanolysis, genetic methods, permethylation, bioinformatic analysis
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 11957 (all data & tools)
• Article ID: 5473
  Zou W, Li J, Vinogradov E, Cox A "Removal of cell wall polysaccharide in pneumococcal capsular polysaccharides by selective degradation via deamination" - Carbohydrate Polymers 218 (2019) 199-207
  

  Pneumococcal cell wall polysaccharide (C-PS), a contaminant in pneumococcal capsular polysaccharide (Pn-PS) vaccines is degraded by mild deamination of the 4-amino-2-acetamido-2,4,6-tri-deoxy-galactose (AAT) in C-PS, which was carried out by addition of 5% aqueous sodium nitrite to a solution of polysaccharide in 5% aqueous acetic acid. Glycosidic linkage and functional groups such as O-acetates, phosphodiesters, and pyruvates were preserved under the conditions. The small fragments from degraded C-PS were removed by ultrafiltration or dialysis to provide essentially C-PS free Pn-PS. Because of the presence of AAT in its structure the deamination is not suitable for the purification of type 1 Pn-PS. Meanwhile, the mass and NMR spectroscopic analysis on the deamination products suggests that both type 1 Pn-PS and C-PS degraded following a major pathway of 5,4-hydride shift, cleavage of AAT O5-C1 bond, C1 hemiacetal formation, and its hydrolysis to release neighboring GalA- in type 1 Pn-PS and GalNAc(6-O-PCho)- in C-PS

  mechanism, degradation, deamination, cell wall polysaccharide, pneumococcal capsular polysaccharide

  NCBI PubMed ID: 31221321
  Publication DOI: 10.1016/j.carbpol.2019.03.070
  Journal NLM ID: 8307156
  Publisher: Elsevier
  Correspondence: W. Zou
  Institutions: Human Health Therapeutic Research Center, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, K1A 0R6, Canada
  Methods: gel filtration, 13C NMR, 1H NMR, sugar analysis, MS/MS, MS, dialysis, SEC-HPLC, ultrafiltration, mild deamination
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 1964 (all data & tools)
• Article ID: 5791
  Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" - Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
  

  Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.

  polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component

  Publication DOI: 10.1016/B978-0-12-819475-1.00005-5
  Publisher: Elsevier
  Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
  Editors: Barchi J, Kamerling H
  Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 7082 (all data & tools)
• Article ID: 6058
  Genning M, Kurbatova EA, Nifantiev NE "Synthetic Analogs of Streptococcus pneumoniae Capsular Polysaccharides and Immunogenic Activities of Glycoconjugates" - Russian Journal of Bioorganic Chemistry 47(1) (2021) 1-25
  

  treptococcus pneumoniae is a Gram-positive bacterium (pneumococcus) that causes severe diseases in adults and children. It was established that some capsular polysaccharides of the clinically significant serotypes of S. pneumoniae in the composition of commercial pneumococcal polysaccharide or conjugate vaccines exhibit low immunogenicity. The review considers production methods and structural features of the synthetic oligosaccharides from the problematic pneumococcal serotypes that are characterized with low immunogenicity due to destruction or detrimental modification occurring in the process of their preparation and purification. Bacterial serotypes that cause severe pneumococcal diseases as well as serotypes not included in the composition of the pneumococcal conjugate vaccines are also discussed. It is demonstrated that the synthetic oligosaccharides corresponding to protective glycotopes of the capsular polysaccharides of various pneumococcal serotypes are capable of inducing formation of the protective opsonizing antibodies and immunological memory. Optimal constructs of oligosaccharides from the epidemiologically significant pneumococcal serotypes are presented that can be used for designing synthetic pneumococcal vaccines, as well as test systems for diagnosis of S. pneumoniae infections and monitoring of vaccination efficiency.

  oligosaccharide, antibodies, ligand, vaccine, immunogen, Opsonophagocytosis, protective activity, pneumococci

  NCBI PubMed ID: 33776393
  Publication DOI: 10.1134/S1068162021010076
  Journal NLM ID: 9420101
  Publisher: Springer Science and Business Media
  Correspondence: nen@ioc.ac.ru
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Mechnikov Research Institute for Vaccines and Sera, 105064 Moscow, Russia
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 7985 (all data & tools)
• Article ID: 6073
  Javed J, Mandal PK "Bacterial surface capsular polysaccharides from Streptococcus pneumoniae: A systematic review on structures, syntheses, and glycoconjugate vaccines" - Carbohydrate Research 502 (2021) 108277
  

  The polysaccharide capsule of Streptococcus pneumoniae constitutes the outermost surface structure of the organism and plays a critical role in virulence. The capsule is the target of current pneumococcal vaccines and glycoconjugates and has important medical and industrial applications. Widespread use of these vaccines is driving changes in serotype prevalence in disease. A massive array of sugars and glycosidic linkages experienced with complete diversity of potential polysaccharide structures. However, it is impossible to collect a sufficient quantity of glycan antigens for the preparation of CPS-based glycoconjugate vaccines from natural sources with high purity and for thorough biological evaluation. So nowadays, the development of a chemical synthetic strategy and their conjugation with a carrier protein to form synthetic glycoconjugate vaccines has been used to gain access on a large scale. This review provides a comprehensive summary of structures, synthesis as well as recent development of synthetic glycoconjugate vaccines, which will support research and may benefit the glycochemical and medical sciences.

  synthesis, Streptococcus pneumoniae, polysaccharides, glycoconjugate vaccines, Pneumococcal Infections

  NCBI PubMed ID: 33743443
  Publication DOI: 10.1016/j.carres.2021.108277
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: P.K. Mandal
  Institutions: Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, P.O. Box 173, Lucknow, 226 031, India, Academy of Scientific and Innovative Research (AcSIR), New Delhi, India
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 5837 (all data & tools)

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Structure type: polymer biological repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_146668,IEDB_146669,IEDB_146671,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

• Article ID: 1013
  Morona JK, Miller DC, Coffey TJ, Vindurampulle CJ, Spratt BG, Morona R, Paton JC "Molecular and genetic characterization of the capsule biosynthesis locus of Streptococcus pneumoniae type 23F" - Microbiology 145(4) (1999) 781-789
  

  The authors have previously reported the nucleotide sequence of the 5' and 3' portions of the Streptococcus pneumoniae type 23F capsular polysaccharide biosynthesis locus (cps23f) (from dexB to cps23fB and from cps23fL to aliA). These regions of cps23f were very similar to the sequence reported for cps19f, the capsule locus of S. pneumoniae type 19F. However, Southern hybridization analysis indicated that no other genes closely related to cps19f are present in the cps23f locus. In this study long-range PCR was used to amplify and clone the section of the S. pneumoniae type 23F capsule locus between cps23fB and cps23fL. This region is 13 kb in size and contains 12 new ORFs, designated cps23fC-E, I, J, and T-Z. Functions are proposed for all of the protein products, including functional homologues of Cps19fC-E, Cps19fI and Cps19fJ. A biosynthetic pathway for type 23F capsular polysaccharide is also proposed.

  biosynthesis, genetic, characterization, Streptococcus, Streptococcus pneumoniae, molecular, locus, type, capsule, capsular polysaccharide biosynthesis, capsule biosynthesis, capsule locus

  NCBI PubMed ID: 10220157
  Journal NLM ID: 0376646
  Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
  Correspondence: patonj@wch.sa.gov.au
  Institutions: Molecular Microbiology Unit, Women's and Children's Hospital, North Adelaide, South Australia 5006, Australia, Wellcome Trust Centre for the Epidemiology of Infectious Disease, Department of Zoology, University of Oxford, Oxford OX1 3PS, UK, Department of Microbiology and Immunology, University of Adelaide, Adelaide, South Australia 5005, Australia
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 3706 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_146668,IEDB_146669,IEDB_146671,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

• Article ID: 1555
  Pujar NS, Huang NF, Daniels CL, Dieter L, Gayton MG, Lee AL "Erratum: Base hydrolysis of phosphodiester bonds in pneumococcal polysaccharides" - Biopolymers 77(6) (2005) 378-379
  

  No abstract

  polysaccharide, Streptococcus, polysaccharides, Research, hydrolysis, phosphodiester, pneumococcal, PDF, P, pneumococcal polysaccharides

  NCBI PubMed ID: 15761954
  Journal NLM ID: 0372525
  Publisher: Wiley Interscience
  Institutions: WP17-301, P. O. Box 4, Merck Research Laboratories, Merck & Co., West Point, PA 19486
  
   
  
  Streptococcus pneumoniae 23F
  CSDB ID 10327 (all data & tools)