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1. Compound ID: 1035
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Gro-(2--P--3)--+
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-4)-b-D-Glcp-(1-4)-b-D-Galp-(1-4)-b-L-Rhap-(1-
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a-L-Rhap-(1-2)-+ |
Show graphically |
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
The structure is contained in the following publication(s):
- 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: 9393802Journal NLM ID: 0246127Publisher: 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
- 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: 15307199Journal NLM ID: 0372525Publisher: Wiley Interscience
Correspondence: hari_pujar@merck.com
Institutions: Merck Research Laboratories, Merck & Co., West Point, PA 19486
- 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: 15093562Journal NLM ID: 8804032Publisher: 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
- 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: 12196537Journal NLM ID: 2985121RPublisher: 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
- 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: 10706792Publication DOI: 10.1006/abio.1999.447Journal NLM ID: 0370535Publisher: Academic Press
Correspondence: abey@merck.com
Institutions: Bioprocess and Bioanalytical Research, Merck Research Laboratories, West Point, Pensylvania, USA
Methods: NMR
- 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: 16087046Publication DOI: 10.1016/j.jpba.2005.01.044Journal NLM ID: 8309336Publisher: London: Elsevier
Institutions: Laboratory for Molecular Structure, National Institute for Biological Standards and Control, South Mimms, UK
Methods: NMR
- 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: 2846013Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
Institutions: Division of Biological Sciences, National Research Council, Ottawa, Ont., Canada
Methods: 13C NMR, 1H NMR
- 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: 8324758Publication DOI: 10.1016/0008-6215(93)84085-kJournal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Biological Chemistry, Merck Research Laboratories, West Point, Pennsylvania
- 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: 0121103Publisher: Kluwer Academic/Plenum Publishers
- 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: 9892037Publisher: Leide, Netherlands: A.W. Sijthoff
- 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: 20810102Publication DOI: 10.1016/j.carres.2010.08.002Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: M. Nitz
Institutions: Department of Chemistry, 80 St. George Str. Toronto, ON, Canada
Methods: NMR, chemical synthesis
- 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: 17009947Publication DOI: 10.1134/S000629790609001XJournal NLM ID: 0376536Publisher: 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
- 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: 26085553Publication DOI: 10.1128/CMR.00024-15Journal NLM ID: 8807282Publisher: 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
- 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: 26169742Publication DOI: 10.1007/978-1-4939-2874-3_12Journal NLM ID: 9214969Publisher: Springer
Correspondence: francesco.x.berti@gsk.com
Institutions: Research, GSK Vaccines, Via Fiorentina 1, 53100, Siena, Italy
- 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: 28837839Publication DOI: 10.1016/j.carres.2017.08.006Journal NLM ID: 0043535Publisher: 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
- 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: 31221321Publication DOI: 10.1016/j.carbpol.2019.03.070Journal NLM ID: 8307156Publisher: 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
- 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/B978-0-12-819475-1.00005-5Publisher: 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
- 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: 33776393Publication DOI: 10.1134/S1068162021010076Journal NLM ID: 9420101Publisher: 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
- 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: 33743443Publication DOI: 10.1016/j.carres.2021.108277Journal NLM ID: 0043535Publisher: 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
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2. Compound ID: 1052
|
D-Gro-(1--P--3)--+
|
-4)-b-D-Glcp-(1-4)-b-D-Galp-(1-4)-b-L-Rhap-(1-
|
a-L-Rhap-(1-2)-+ |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130695,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_146668,IEDB_146671,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 300
Lee CH, Frasch CE "Quantification of bacterial polysaccharides by the purpald assay: Measurement of periodate-generated formaldehyde from glycol in the repeating unit" -
Analytical Biochemistry 296(1) (2001) 73-82
We have adapted the purpald assay for measurement of bacterial polysaccharides (PS) containing substituted and/or unsubstituted glycol (SG or UG) in residues such as glycerol, ribitol, arabinitol, furanosyl galactose, and sialyl. For the purpald assay of UG-containing PS, 50 microL of PS samples was consecutively reacted with 50 microL of 16 mM NaIO4 for 20 min, 50 microL of 136 mM purpald reagent in 2 N NaOH for 20 min, and 50 microL of 64 mM NaIO4 for 20 min in a 96-well tissue culture plate followed by a measurement of absorbance at 550 nm with a plate reader. For SG-containing PS, conversion of SG to UG with 25 micro;L of 0.3 N NaOH, 1 h at room temperature for de-O-acetylation followed by 25 microL of 0.6 M H2SO4, 1 h at 80 degrees C for acid hydrolysis of PS precedes the periodate treatment in the purpald assay. The concentration of the samples can be calculated from the sample absorbance and the reference standard curve constructed from the reference concentrations of the same PS (well-characterized) and their corresponding absorbance values assayed in the same plate. The purpald assay provides a tool in addition to the existing ones for the measurement of glycol-containing PS. Among the usefulness of this method are the determinations of the glycerol content in the phospho-glycerol-containing PS and the SG and UG contents and structural integrity in PS and conjugate vaccines.
repeating unit, bacterial polysaccharides, quantification
NCBI PubMed ID: 11520034Publication DOI: 10.1006/abio.2001.5230Journal NLM ID: 0370535Publisher: Academic Press
Institutions: Laboratory of Bacterial Polysaccharides, Division of Bacterial, Parasitic and Allergenic Products, OVRR, CBER, FDA, 8800 Rockville Pike, Bethesda, MD, USA
Methods: purpald assay measurement
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3. Compound ID: 2888
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Gro-(2--P--3)--+
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-4)-b-D-Galp-(1-4)-b-L-Rhap-(1-4)-b-D-Glcp-(1-
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a-L-Rhap-(1-2)-+ |
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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
The structure is contained in the following publication(s):
- 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: 10220157Journal NLM ID: 0376646Publisher: 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
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4. Compound ID: 4195
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D-Gro-(2--P--3)--+
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-4)-b-D-Glcp-(1-4)-b-D-Galp-(1-4)-b-L-Rhap-(1-
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a-L-Rhap-(1-2)-+ |
Show graphically |
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
The structure is contained in the following publication(s):
- 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: 15761954Journal NLM ID: 0372525Publisher: Wiley Interscience
Institutions: WP17-301, P. O. Box 4, Merck Research Laboratories, Merck & Co., West Point, PA 19486
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5. Compound ID: 5117
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a-L-Rhap-(1-2)-+
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P-3)-+ |
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-4)-b-D-Glcp-(1-4)-b-D-Galp-(1-4)-b-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: polysaccharide S23 (Merck, Sharp and Dohme)
Compound class: CPS
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_146668,IEDB_146670,IEDB_146671,IEDB_146672,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 2043
Jones C "Identification of the tetrasaccharide repeating-unit of the Streptococcus pneumoniae type 23 polysaccharide by high-field proton NMR spectroscopy" -
Carbohydrate Research 139 (1985) 75-83
Journal NLM ID: 0043535Publisher: Elsevier
Methods: 1H NMR
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6. Compound ID: 5118
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a-L-Rhap-(1-2)-+
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-4)-b-D-Glcp-(1-4)-b-D-Galp-(1-4)-b-L-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: polysaccharide S23 (Merck, Sharp and Dohme)
Compound class: CPS
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_146668,IEDB_146671,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 2043
Jones C "Identification of the tetrasaccharide repeating-unit of the Streptococcus pneumoniae type 23 polysaccharide by high-field proton NMR spectroscopy" -
Carbohydrate Research 139 (1985) 75-83
Journal NLM ID: 0043535Publisher: Elsevier
Methods: 1H NMR
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7. Compound ID: 5802
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P-2)-Gro-(1-3)-+
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-4)-b-D-Glcp-(1-4)-b-D-Galp-(1-4)-b-L-Rhap-(1-
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a-L-Rhap-(1-2)-+ |
Show graphically |
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_146671,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 2549
Alonso de Velasco E, Verheul AFM, van Steijn AMP, Dekker HAT, Feldman RG, Fernandez IM, Kamerling JP, Vliegenthart JFG, Verhoef J, Snippe H "Epitope specificity of rabbit IgG elicited by pneumococcal type 23F synthetic oligosaccharide- and native polysaccharide-protein conjugate vaccines: comparison with human anti-polysaccharide 23F IgG" -
Infection and Immunity 62 (1994) 799-808
Streptococcus pneumoniae type 23F capsular polysaccharide (PS23F) consitss of a repeating glycerol-phosphorylated branched tetrasaccharide. The immunogenicities of the following related antigens were investigated: (i) a synthetic trisaccharide comprising the backbone of one repeating unit, (ii) a synthetic tetrasaccharide comprising the complete repeating unit, and (iii) native PS23F (all three conjugated to keyhole limpet hemocyanin [KLH]) and (iv) formalin-killed S. pneumoniae 23F. All antigens except the trisaccharide-KLH conjugate induced relatively high anti-PS23F antibody levels in rabbits. The epitope specificity of such antibodies was then studied by means of an inhibition immunoassay. The α(1→2)-linked L-rhamnose branch was shown to be immunodominant for immunoglobulin G (IgG) induced by tetrasaccharide-KLH, PS23F-KLH, and killed S. pneumoniae 23F: in most sera L-rhamnose totally inhibited the binding of IgG to PS23F. Thus, there appears to be no major difference in epitope specificity between IgG induced by tetrasaccharide-KLH and that induced by antigens containing the polymeric form of PS23F. Human anti-PS23F IgG (either vaccine induced or naturally acquired) had a different epitope specificity: none of the inhibitors used, including L-rhamnose and tetrasaccharide-KLH, exhibited substantial inhibition. These observations suggest that the epitope recognized by human IgG on PS23F is larger than the epitope recognized by rabbit IgG. Both human and rabbit antisera efficiently opsonized type 23F pneumococci, as measured in a phagocytosis assay using human polymorphonuclear leukocytes.
NCBI PubMed ID: 7509318Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: Eijkman-Winkler Laboratory of Medical Microbiology, Utrecht University, Utrecht, The Netherlands
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8. Compound ID: 12666
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a-L-Rhap-(1-2)-+
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Gro-(2--P--3)--b-D-Galp-(1-4)-+
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-4)-b-D-Glcp-(1-3)-b-L-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_146671,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- 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: 28837839Publication DOI: 10.1016/j.carres.2017.08.006Journal NLM ID: 0043535Publisher: 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
- 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/B978-0-12-819475-1.00005-5Publisher: 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
- 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: 33743443Publication DOI: 10.1016/j.carres.2021.108277Journal NLM ID: 0043535Publisher: 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
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