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1. Compound ID: 230
b-D-GlcpA-(1-4)-+ R-Pyr-(2-6:2-4)-+
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-3)-b-D-Galp-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_115013,IEDB_115136,IEDB_130645,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_138950,IEDB_140630,IEDB_141495,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_190606,IEDB_423153,IEDB_742249,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 57
Erbing B, Jansson P, Widmalm G, Nimmich W "Structure of the capsular polysaccharide from the Klebsiella K8 reference strain 1015" -
Carbohydrate Research 273(2) (1995) 197-205
The structure of the capsular polysaccharide from the Klebsiella K8 reference strain 1015 has been elucidated. The structure was deduced from sugar analysis, different methylation analyses, a uronic acid degradation, and NMR spectroscopy. It is concluded that the polysaccharide is composed of pentasaccharide repeating units with the structure: [formula: see text] The structure differs from that of the previously published structure of the capsular polysaccharide from Klebsiella K8, which originates from another strain and has the following structure: [formula: see text] The serological similarity between the two strains is most likely derived from a common tetrasaccharide which is substituted in different ways in the two strains. Since the strain in the present investigation originates from the Klebsiella K reference strain collection of the International Escherichia and Klebsiella Centre, Copenhagen, Denmark, it is suggested that it should keep the designation K8. The other polysaccharide with Klebsiella K8 specificity should be renamed as K8,52,59 based on the cross-reactivity of the strain (I. Orskov, unpublished)
structure, strain, structural, capsular, polysaccharide, capsular polysaccharide, type, Klebsiella, pyruvate acetal, reference
NCBI PubMed ID: 8565007Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden, Clinical Research Centre, Analytical Unit, Karolinska Institutet, Huddinge Hospital, Novum, S-141 86 Huddinge, Sweden, Institut fiir Medizinische Mikrobiologie, Universitiit Rostock, D-18055 Rostock, Germany
- Article ID: 6301
Qin CJ, Ding MR, Tian GZ, Zou XP, Fu JJ, Hu J, Yin J "Chemical approaches towards installation of rare functional groups in bacterial surface glycans" -
Chinese Journal of Natural Medicines = Zhongguo Tianran Yaowu 20(6) (2022) 401-420
Bacterial surface glycans perform a diverse and important set of biological roles, and have been widely used in the treatment of bacterial infectious diseases. The majority of bacterial surface glycans are decorated with diverse rare functional groups, including amido, acetamidino, carboxamido and pyruvate groups. These functional groups are thought to be important constituents for the biological activities of glycans. Chemical synthesis of glycans bearing these functional groups or their variants is essential for the investigation of structure-activity relationships by a medicinal chemistry approach. To date, a broad choice of synthetic methods is available for targeting the different rare functional groups in bacterial surface glycans. This article reviews the structures of naturally occurring rare functional groups in bacterial surface glycans, and the chemical methods used for installation of these groups.
chemical synthesis, acetamidino group, amido group, bacterial surface glycan, carboxamido group, pyruvyl ketal
NCBI PubMed ID: 35750381Publication DOI: 10.1016/S1875-5364(22)60177-8Journal NLM ID: 101504416Publisher: Beijing: Science Press; Elsevier
Correspondence: J. Yin
Institutions: Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, China, Wuxi School of Medicine, Jiangnan University, Wuxi, China
- Article ID: 12675
Kelly SD, Ovchinnikova OG, Muller F, Steffen M, Braun M, Sweeney RP, Kowarik M, Follador R, Lowary TL, Serventi F, Whitfield C "Identification of a second glycoform of the clinically prevalent O1 antigen from Klebsiella pneumoniae" -
Proceedings of the National Academy of Sciences of the USA 120(29) (2023) e2301302120
Carbapenemase and extended beta-lactamase-producing Klebsiella pneumoniae isolates represent a major health threat, stimulating increasing interest in immunotherapeutic approaches for combating Klebsiella infections. Lipopolysaccharide O antigen polysaccharides offer viable targets for immunotherapeutic development, and several studies have described protection with O-specific antibodies in animal models of infection. O1 antigen is produced by almost half of clinical Klebsiella isolates. The O1 polysaccharide backbone structure is known, but monoclonal antibodies raised against the O1 antigen showed varying reactivity against different isolates that could not be explained by the known structure. Reinvestigation of the structure by NMR spectroscopy revealed the presence of the reported polysaccharide backbone (glycoform O1a), as well as a previously unknown O1b glycoform composed of the O1a backbone modified with a terminal pyruvate group. The activity of the responsible pyruvyltransferase (WbbZ) was confirmed by western immunoblotting and in vitro chemoenzymatic synthesis of the O1b terminus. Bioinformatic data indicate that almost all O1 isolates possess genes required to produce both glycoforms. We describe the presence of O1ab-biosynthesis genes in other bacterial species and report a functional O1 locus on a bacteriophage genome. Homologs of wbbZ are widespread in genetic loci for the assembly of unrelated glycostructures in bacteria and yeast. In K. pneumoniae, simultaneous production of both O1 glycoforms is enabled by the lack of specificity of the ABC transporter that exports the nascent glycan, and the data reported here provide mechanistic understanding of the capacity for evolution of antigenic diversity within an important class of biomolecules produced by many bacteria.
Lipopolysaccharide, O antigen, Klebsiella pneumoniae, antigenic diversity, vaccine candidate
NCBI PubMed ID: 37428935Publication DOI: 10.1073/pnas.2301302120Journal NLM ID: 7505876Publisher: National Academy of Sciences
Correspondence: F. Serventi
; C. Whitfield
Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, ON N1G 2W1, Canada, LimmaTech Biologics AG, Schlieren 8952, Switzerland, Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada, Institute of Biological Chemistry, Academia Sinica, Taipei, Nangang 11529, Taiwan, Institute of Biochemical Sciences, National Taiwan University, Taipei 10617, Taiwan
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, ESI-MS, mild acid hydrolysis, Western blotting, genetic methods, enzyme assay, LC-MS, bioinformatic analysis, SEC, phylogenetic analysis, monoclonal antibodies
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2. Compound ID: 1045
D-Gro-(1--P--4)--+
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-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-a-D-Glcp2Ac3Ac-(1-4)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130695,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_138950,IEDB_141495,IEDB_141794,IEDB_141806,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_190606,IEDB_742249,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_61,SB_7,SB_87,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
- 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
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3. Compound ID: 1360
a-D-GlcpNAc-(1-2)-L-gro-a-D-manHepp-(1-3)-+ a-Kdop-(2-4)-+
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a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Trivial name: lipooligosaccharide core L1 / L10
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130650,IEDB_130659,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_138950,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_141495,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_226300,IEDB_418767,IEDB_418769,IEDB_419429,IEDB_742249,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 432
Zhu P, Klutch MJ, Bash MC, Tsang RS, Ng LK, Tsai CM "Genetic diversity of three lgt loci for biosynthesis of lipooligosaccharide (LOS) in Neisseria species" -
Microbiology 148(6) (2002) 1833-1844
Lipooligosaccharide (LOS) is a major virulence factor of the pathogenic NEISSERIA: Nine lgt genes at three chromosomal loci (lgt-1, 2, 3) encoding the glycosyltransferases responsible for the biosynthesis of LOS oligosaccharide chains were examined in 26 Neisseria meningitidis, 51 Neisseria gonorrhoeae and 18 commensal Neisseria strains. DNA hybridization, PCR and nucleotide sequence data were compared to previously reported lgt genes. Analysis of the genetic organization of the lgt loci revealed that in N. meningitidis, the lgt-1 and lgt-3 loci were hypervariable genomic regions, whereas the lgt-2 locus was conserved. In N. gonorrhoeae, no variability in the composition or organization of the three lgt loci was observed. lgt genes were detected only in some commensal Neisseria species. The genetic organization of the lgt-1 locus was classified into eight types and the lgt-3 locus was classified into four types. Two types of arrangement at lgt-1 (II and IV) and one type of arrangement at lgt-3 (IV) were novel genetic organizations reported in this study. Based on the three lgt loci, 10 LOS genotypes of N. meningitidis were distinguished. Phylogenetic analysis revealed a gene cluster, lgtH, which separated from the homologous genes lgtB and lgtE. The lgtH and lgtE genes were mutually exclusive and were located at the same position in lgt-1. The data demonstrated that pathogenic and commensal Neisseria share a common lgt gene pool and horizontal gene transfer appears to contribute to the genetic diversity of the lgt loci in Neisseria
biosynthesis, oligosaccharide structure, Neisseria meningitidis, Neisseria, gene cluster, glycosyltransferases, Gonorrhoeae, Neisseria gonorrhoeae, genetic diversity, lipooligosaccharide (LOS), phylogenetic analysis, virulence factor
NCBI PubMed ID: 12055303Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: zhu@cber.fda.gov
Institutions: Division of Bacterial, Parasitic and Allergenic Products and Division of Viral Products, Center for Biologics Evaluation and Research, FDA, 8800 Rockville Pike, Bethesda, MD, USA
Methods: PCR, DNA sequencing, DNA techniques, genetic methods, RT-PCR
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4. Compound ID: 3343
b-D-Glcp-(1-6)-+
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-4)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-a-IdopA-(1-3)-b-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130648,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_138950,IEDB_141495,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_190606,IEDB_742249,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_25,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1231
Sheng S, Cherniak R "Structure of the capsular polysaccharide of Clostridium perfringens Hobbs 10 determined by NMR spectroscopy" -
Carbohydrate Research 305(1) (1997) 65-72
The complete primary structure of the type-specific capsular polysaccharide of Clostridium perfringens Hobbs 10 was determined. The polysaccharide was isolated from C. perfringens Hobbs 10 by cold-water extraction of whole, heavily encapsulated cells. The polysaccharide was purified, by ethanol precipitation, deproteination, selective precipitation with hexadecyltrimethylammonium bromide, ion-exchange chromatography and gel-filtration chromatography. The polysaccharide was comprised of D-glucose, D-galactose, N-acetylgalactosamine, and iduronic acid, in molar ratios of 2:2:1:1. Sequence and linkage assignments of the glycosyl residues were obtained by NMR spectroscopy, specifically by the combination of two-dimensional homonuclear DQF-COSY, TQF-COSY and TOCSY, heteronuclear ¿1H, 13C¿ single-quantum coherence (HSQC) and heteronuclear multiple-bond correlation (HMBC) experiments. The capsular polysaccharide of C. perfringens Hobbs 10 is a polymer composed of a hexasaccharide repeating unit with the following structure: [formula: see text] This structure is novel among bacterial cell-surface polysaccharides, and it is only the second of many serotypically distinct capsular polysaccharides of C. perfringens to be described.
antigen, polysaccharide structure, 2D NMR spectroscopy, HMBC, TOCSY, Clostridium perfringens, DQF-COSY, TQF-COSY, HSQC
NCBI PubMed ID: 9534227Publication DOI: 10.1016/S0008-6215(97)00280-2Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: cherniak@gsu.edu
Institutions: Department of Chemistry,Georgia State Univetsity, Atlanta,USA
Methods: NMR
- 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
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5. Compound ID: 3374
b-D-Galp-(1-6)-+
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-6)-b-D-Galp-(1-4)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-b-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_138950,IEDB_141495,IEDB_141794,IEDB_141806,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_153201,IEDB_156493,IEDB_190606,IEDB_241101,IEDB_742249,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1251
Staaf M, Widmalm G, Yang Z, Huttunen E "Structural elucidation of an extracellular polysaccharide produced by Lactobacillus helveticus" -
Carbohydrate Research 291 (1996) 155-164
An extracellular polysaccharide produced by a strain of Lactobacillus helveticus isolated from cheese milk has been investigated. Sugar and methylation analysis together with 1H and 13C NMR spectroscopy revealed that the polysaccharide is composed of hexasaccharide repeating units. The sequence of sugar residues was determined by use of two-dimensional nuclear Overhauser effect spectroscopy and heteronuclear multiple-bond correlation experiments. The structure of the repeating unit of the exopolysaccharide from L. helveticus is as follows: [sequence: see text]
NMR, structure, structural, polysaccharide, determination, NMR spectroscopy, exopolysaccharide, Lactobacillus helveticus, extracellular polysaccharide, spectroscopy, elucidation, Lactobacillus, extracellular, D-glucose, D-galactose
NCBI PubMed ID: 8864228Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, S-10691, Sweden, Department of Food Technology, Dairy Science, University of Helsinki, Helsinki, Finland
Methods: NMR-2D, methylation, NMR
- 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: 6264
Lebrilla CB, Liu J, Widmalm G, Prestegard JH "Oligosaccharides and Polysaccharides" -
Book: Essentials of Glycobiology [Internet]. 4rd edition. (2022)
This chapter discusses the diversity in structure and properties that results when multiple monosaccharides (Chapter 2) are linked together to form oligosaccharides and polysaccharides (the latter comprising much of the biomass on the planet). Some examples of the more complex polymeric assemblies that occur in nature are presented, and how these remarkable structures are generated is discussed.
structure, polysaccharide, polysaccharides, Oligosaccharides
NCBI PubMed ID: 35536971Publication DOI: 10.1101/glycobiology.4e.3Publisher: Cold Spring Harbor (NY): Cold Spring Harbor Laboratory Press
Editors: Varki A, Cummings RD, Esko JD, Stanley P, Hart GW, Aebi M, Mohnen D, Kinoshita T, Packer NH, Prestegard JH, Schnaar RL, Seeberger RH
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6. Compound ID: 3590
D-Gro-(1--P--4)--+
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-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-a-D-Glc-(1-4)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130695,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_138950,IEDB_141495,IEDB_141794,IEDB_141806,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_190606,IEDB_742249,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- 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
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7. Compound ID: 4194
D-Gro-(1--P--4)--+
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-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-a-D-Glcp3Ac-(1-4)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130695,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_138950,IEDB_141495,IEDB_141794,IEDB_141806,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_190606,IEDB_742249,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_87,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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8. Compound ID: 4312
a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-D-manHepp-(1--/rest of core-lipid A/ |
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Structure type: oligomer
Aglycon: rest of core-lipid A
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_138950,IEDB_140087,IEDB_141495,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_190606,IEDB_2189047,IEDB_742249,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1616
Gulati S, Cox A, Lewis LA, Michael FS, Li J, Boden R, Ram S, Rice PA "Enhanced factor H binding to sialylated gonococci is restricted to the sialylated lacto-N-neotetraose lipooligosaccharide species: implications for serum resistance and evidence for a bifunctional lipooligosaccharide sialyltransferase in gonococci" -
Infection and Immunity 73(11) (2005) 7390-7397
We isolated serologically identical (by serovar determination and porin variable region [VR] typing) strains of Neisseria gonorrhoeae from an infected male and two of his monogamous female sex partners. One strain (termed 398078) expressed the L1 (Gal α1→3 Gal β1→4 Glc β1→4 HepI) lipooligosaccharide (LOS) structure exclusively; the other (termed 398079) expressed the lacto-N-neotetraose (LNT; Gal β1→4 GlcNAc β1→3 Gal β1→4 Glc β1→4 HepI) LOS structure. The strain from the male index case expressed both glycoforms and exhibited both immunotypes. Nuclear magnetic resonance analysis revealed that sialic acid linked to the terminal Gal of L1 LOS via an α2→6 linkage and, as expected, to the terminal Gal of LNT LOS via an α2→3 linkage. Insertional inactivation of the sialyltransferase gene (known to sialylate LNT LOS) abrogated both L1 LOS sialylation and LNT LOS sialylation, suggesting a bifunctional nature of this enzyme in gonococci. Akin to our previous observations, sialylation of the LNT LOS of strain 398079 enhanced the binding of the complement regulatory molecule, factor H. Rather surprisingly, factor H did not bind to sialylated strain 398078. LOS sialylation conferred the LNT LOS-bearing strain complete (100%) resistance to killing by even 50% nonimmune normal human serum (NHS), whereas sialylation of L1 LOS conferred resistance only to 10% NHS. The ability of gonococcal sialylated LNT to bind factor H confers high-level serum resistance, which is not seen with sialylated L1 LOS. Thus, serum resistance mediated by sialylation of gonococcal L1 and LNT LOS occurs by different mechanisms, and specificity of factor H binding to sialylated gonococci is restricted to the LNT LOS species.
Lipooligosaccharide, enhanced, factor, sialyltransferase, binding, lacto-N-neotetraose, resistance, serum, serum resistance, species, Lewis, sialylated, implication, gonococci
NCBI PubMed ID: 16239538Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: National Research Council, Ottawa, ON K1A 0R6, Canada, Division of Infectious Diseases and Immunology, University of Massachusetts Medical School, Worcester, Massachusetts 016051, Evans Biomedical Research Center, Boston University Medical Center, Boston, Massachusetts 021183
Methods: NMR, MS
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9. Compound ID: 4314
Neup5Ac-(2-6)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-D-manHepp-(1--/rest of core-lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: rest of core-lipid A
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_136044,IEDB_136794,IEDB_136906,IEDB_137472,IEDB_138950,IEDB_140087,IEDB_141495,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_149558,IEDB_151528,IEDB_158551,IEDB_190606,IEDB_2189047,IEDB_423085,IEDB_742249,IEDB_918314,IEDB_983931,SB_126,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_6,SB_7,SB_84,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1616
Gulati S, Cox A, Lewis LA, Michael FS, Li J, Boden R, Ram S, Rice PA "Enhanced factor H binding to sialylated gonococci is restricted to the sialylated lacto-N-neotetraose lipooligosaccharide species: implications for serum resistance and evidence for a bifunctional lipooligosaccharide sialyltransferase in gonococci" -
Infection and Immunity 73(11) (2005) 7390-7397
We isolated serologically identical (by serovar determination and porin variable region [VR] typing) strains of Neisseria gonorrhoeae from an infected male and two of his monogamous female sex partners. One strain (termed 398078) expressed the L1 (Gal α1→3 Gal β1→4 Glc β1→4 HepI) lipooligosaccharide (LOS) structure exclusively; the other (termed 398079) expressed the lacto-N-neotetraose (LNT; Gal β1→4 GlcNAc β1→3 Gal β1→4 Glc β1→4 HepI) LOS structure. The strain from the male index case expressed both glycoforms and exhibited both immunotypes. Nuclear magnetic resonance analysis revealed that sialic acid linked to the terminal Gal of L1 LOS via an α2→6 linkage and, as expected, to the terminal Gal of LNT LOS via an α2→3 linkage. Insertional inactivation of the sialyltransferase gene (known to sialylate LNT LOS) abrogated both L1 LOS sialylation and LNT LOS sialylation, suggesting a bifunctional nature of this enzyme in gonococci. Akin to our previous observations, sialylation of the LNT LOS of strain 398079 enhanced the binding of the complement regulatory molecule, factor H. Rather surprisingly, factor H did not bind to sialylated strain 398078. LOS sialylation conferred the LNT LOS-bearing strain complete (100%) resistance to killing by even 50% nonimmune normal human serum (NHS), whereas sialylation of L1 LOS conferred resistance only to 10% NHS. The ability of gonococcal sialylated LNT to bind factor H confers high-level serum resistance, which is not seen with sialylated L1 LOS. Thus, serum resistance mediated by sialylation of gonococcal L1 and LNT LOS occurs by different mechanisms, and specificity of factor H binding to sialylated gonococci is restricted to the LNT LOS species.
Lipooligosaccharide, enhanced, factor, sialyltransferase, binding, lacto-N-neotetraose, resistance, serum, serum resistance, species, Lewis, sialylated, implication, gonococci
NCBI PubMed ID: 16239538Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: National Research Council, Ottawa, ON K1A 0R6, Canada, Division of Infectious Diseases and Immunology, University of Massachusetts Medical School, Worcester, Massachusetts 016051, Evans Biomedical Research Center, Boston University Medical Center, Boston, Massachusetts 021183
Methods: NMR, MS
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10. Compound ID: 4514
Gro-(1--P--4)--+
|
-3)-b-D-Galp-(1-4)-a-D-Glcp-(1-6)-a-D-Glcp2Ac-(1-4)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130695,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141495,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_190606,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_61,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1729
Kennedy DA, Buchanan JG, Baddiley J "The type-specific substance from Pneumococcus type 11A(43)" -
Biochemical Journal 115 (1969) 37-45
Journal NLM ID: 2984726RPublisher: London, UK : Published by Portland Press on behalf of the Biochemical Society
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11. Compound ID: 4952
Gro-(1--P--4)--+
|
-3)-b-D-Galp-(1-4)-a-D-Glcp-(1-6)-a-D-Glcp-(1-4)-a-D-Galp-(1-
|
/Variants 0/-+
/Variants 0/ is:
Ac-3)-
OR (exclusively)
Ac-2)- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130695,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141495,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_190606,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_61,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1912
Richards JC, Perry MB, Kniskern PJ "The structure of the specific capsular polysaccharide of Streptococcus pneumoniae type 11F (American type 11)" -
Canadian Journal of Biochemistry and Cell Biology = Revue canadienne de biochimie et biologie cellulaire 63(12) (1985) 953-968
The specific polysaccharide of Streptococcus pneumoniae type 11F (American type 11) is composed of 2-acetamido-2-deoxy-D-glucose (one part), D-glucose (one part), D-galactose (two parts), ribitol (one part), phosphate (one part), and O-acetyl (two parts). Hydrolysis, dephosphorylation, periodate oxidation, methylation, optical rotation, and 1H and 13C nuclear magnetic resonance studies showed that the polysaccharide is an unbranched linear polymer of a ribitol-phosphate substituted repeating tetrasaccharide unit having the structure: (Formula: see text). The specific capsular polysaccharides of S. pneumoniae type 11B and 11C (American types 76 and 53) were found to have the same tetrasaccharide repeating unit as the 11F polysaccharide, but differed from it in their mode of O-acetylation and the replacement of the ribitol phosphate by glycerol phosphate in the 11C specific polysaccharide.
NCBI PubMed ID: 4075231Publication DOI: 10.1139/o85-118Journal NLM ID: 8302763Publisher: Ottawa: National Research Council Of Canada
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario K1A OR6 Canada, Merck Sharp & Dohme Research Laboratories, West Point, PA, U.S.A. 19486
Methods: gel filtration, 13C NMR, 1H NMR, methylation, GLC-MS, sugar analysis, dephosphorylation, TLC, GLC, paper chromatography, de-O-acetylation, ion-exchange chromatography, immunodiffusion assays, periodate oxidation, optical rotation measurement
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12. Compound ID: 4953
Rib-ol-(1--P--4)--+
|
-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-a-D-GlcpNAc3Ac-(1-4)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_114703,IEDB_115013,IEDB_130645,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_138950,IEDB_141495,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_742249,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1912
Richards JC, Perry MB, Kniskern PJ "The structure of the specific capsular polysaccharide of Streptococcus pneumoniae type 11F (American type 11)" -
Canadian Journal of Biochemistry and Cell Biology = Revue canadienne de biochimie et biologie cellulaire 63(12) (1985) 953-968
The specific polysaccharide of Streptococcus pneumoniae type 11F (American type 11) is composed of 2-acetamido-2-deoxy-D-glucose (one part), D-glucose (one part), D-galactose (two parts), ribitol (one part), phosphate (one part), and O-acetyl (two parts). Hydrolysis, dephosphorylation, periodate oxidation, methylation, optical rotation, and 1H and 13C nuclear magnetic resonance studies showed that the polysaccharide is an unbranched linear polymer of a ribitol-phosphate substituted repeating tetrasaccharide unit having the structure: (Formula: see text). The specific capsular polysaccharides of S. pneumoniae type 11B and 11C (American types 76 and 53) were found to have the same tetrasaccharide repeating unit as the 11F polysaccharide, but differed from it in their mode of O-acetylation and the replacement of the ribitol phosphate by glycerol phosphate in the 11C specific polysaccharide.
NCBI PubMed ID: 4075231Publication DOI: 10.1139/o85-118Journal NLM ID: 8302763Publisher: Ottawa: National Research Council Of Canada
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario K1A OR6 Canada, Merck Sharp & Dohme Research Laboratories, West Point, PA, U.S.A. 19486
Methods: gel filtration, 13C NMR, 1H NMR, methylation, GLC-MS, sugar analysis, dephosphorylation, TLC, GLC, paper chromatography, de-O-acetylation, ion-exchange chromatography, immunodiffusion assays, periodate oxidation, optical rotation measurement
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13. Compound ID: 4954
Gro-(1--P--4)--+
|
-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-a-D-GlcpNAc3Ac-(1-4)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130695,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_138950,IEDB_141495,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_742249,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1912
Richards JC, Perry MB, Kniskern PJ "The structure of the specific capsular polysaccharide of Streptococcus pneumoniae type 11F (American type 11)" -
Canadian Journal of Biochemistry and Cell Biology = Revue canadienne de biochimie et biologie cellulaire 63(12) (1985) 953-968
The specific polysaccharide of Streptococcus pneumoniae type 11F (American type 11) is composed of 2-acetamido-2-deoxy-D-glucose (one part), D-glucose (one part), D-galactose (two parts), ribitol (one part), phosphate (one part), and O-acetyl (two parts). Hydrolysis, dephosphorylation, periodate oxidation, methylation, optical rotation, and 1H and 13C nuclear magnetic resonance studies showed that the polysaccharide is an unbranched linear polymer of a ribitol-phosphate substituted repeating tetrasaccharide unit having the structure: (Formula: see text). The specific capsular polysaccharides of S. pneumoniae type 11B and 11C (American types 76 and 53) were found to have the same tetrasaccharide repeating unit as the 11F polysaccharide, but differed from it in their mode of O-acetylation and the replacement of the ribitol phosphate by glycerol phosphate in the 11C specific polysaccharide.
NCBI PubMed ID: 4075231Publication DOI: 10.1139/o85-118Journal NLM ID: 8302763Publisher: Ottawa: National Research Council Of Canada
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario K1A OR6 Canada, Merck Sharp & Dohme Research Laboratories, West Point, PA, U.S.A. 19486
Methods: gel filtration, 13C NMR, 1H NMR, methylation, GLC-MS, sugar analysis, dephosphorylation, TLC, GLC, paper chromatography, de-O-acetylation, ion-exchange chromatography, immunodiffusion assays, periodate oxidation, optical rotation measurement
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14. Compound ID: 4955
Rib-ol-(1--P--4)--+
|
-6)-a-D-GlcpNAc-(1-4)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_114703,IEDB_115013,IEDB_130645,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_138950,IEDB_141495,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_742249,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1912
Richards JC, Perry MB, Kniskern PJ "The structure of the specific capsular polysaccharide of Streptococcus pneumoniae type 11F (American type 11)" -
Canadian Journal of Biochemistry and Cell Biology = Revue canadienne de biochimie et biologie cellulaire 63(12) (1985) 953-968
The specific polysaccharide of Streptococcus pneumoniae type 11F (American type 11) is composed of 2-acetamido-2-deoxy-D-glucose (one part), D-glucose (one part), D-galactose (two parts), ribitol (one part), phosphate (one part), and O-acetyl (two parts). Hydrolysis, dephosphorylation, periodate oxidation, methylation, optical rotation, and 1H and 13C nuclear magnetic resonance studies showed that the polysaccharide is an unbranched linear polymer of a ribitol-phosphate substituted repeating tetrasaccharide unit having the structure: (Formula: see text). The specific capsular polysaccharides of S. pneumoniae type 11B and 11C (American types 76 and 53) were found to have the same tetrasaccharide repeating unit as the 11F polysaccharide, but differed from it in their mode of O-acetylation and the replacement of the ribitol phosphate by glycerol phosphate in the 11C specific polysaccharide.
NCBI PubMed ID: 4075231Publication DOI: 10.1139/o85-118Journal NLM ID: 8302763Publisher: Ottawa: National Research Council Of Canada
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario K1A OR6 Canada, Merck Sharp & Dohme Research Laboratories, West Point, PA, U.S.A. 19486
Methods: gel filtration, 13C NMR, 1H NMR, methylation, GLC-MS, sugar analysis, dephosphorylation, TLC, GLC, paper chromatography, de-O-acetylation, ion-exchange chromatography, immunodiffusion assays, periodate oxidation, optical rotation measurement
- Article ID: 4833
Calix JJ, Nahm MH, Zartler ER "Elucidation of structural and antigenic properties of pneumococcal serotype 11A, 11B, 11C, and 11F polysaccharide capsules" -
Journal of Bacteriology 193(19) (2011) 5271-5278
Despite the emerging impact of serogroup 11 serotypes in Streptococcus pneumoniae epidemiology, the structures of serogroup 11 capsule types have not been fully elucidated, particularly the locations of O-acetyl substitutions. Here, we report the complete structures of the serotype 11B, 11C, and 11F polysaccharides and a revision to the serotype 11A capsular polysaccharide using nuclear magnetic resonance (NMR). All structures shared a linear, tetrasaccharide backbone with a pendant phosphopolyalcohol. Three of four saccharides are conserved in all serotypes. The individual serotype capsules differed in the identity of one saccharide, the pendant phosphopolyalcohol, and the O-acetylation pattern. Though the assigned locations of O-acetate substitutions in this study differed from those of previous reports, our findings were corroborated with strong correlations to serology and genetics. We examined the binding of serotyping sera to serogroup 11 polysaccharides by using flow cytometry and an inhibition-type enzyme-linked immunosorbent assay (ELISA) and found that de-O-acetylation of capsular polysaccharides by mild hydrolysis decreases its immunoreactivity, supporting the crucial role of O-acetylation in the antigenicity of these polysaccharides. Due to strong correlations between polysaccharide structures and capsule biosynthesis genes, we were able to assign target substrates for the O-acetyltransferases encoded by wcwC, wcwR, wcwT, and wcjE. We identified antigenic determinants for serogroup 11 serotyping sera and highlight the idea that conventional serotyping methods are not capable of recognizing all putative variants of S. pneumoniae serogroup 11.
serotype, Streptococcus pneumoniae, capsular polysaccharides, O-acetylation, capsule
NCBI PubMed ID: 21803987Publication DOI: 10.1128/JB.05034-11Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: Edward_zartler@merck.com
Institutions: Department of Pathology, Department of Microbiology, University of Alabama at Birmingham, Birmingham, AL, USA, Vaccine Analytical Development, Merck Research Laboratories, Merck and Company, West Point, Pennsylvania
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, ELISA, 31P NMR, de-O-acetylation, NMR-1D, serological methods
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15. Compound ID: 4956
Rib3(50%)Ac-ol-(1--P--4)--+
|
-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-a-D-GlcpNAc-(1-4)-a-D-Galp2Ac-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_114703,IEDB_115013,IEDB_130645,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_138950,IEDB_141495,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_742249,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_36,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1912
Richards JC, Perry MB, Kniskern PJ "The structure of the specific capsular polysaccharide of Streptococcus pneumoniae type 11F (American type 11)" -
Canadian Journal of Biochemistry and Cell Biology = Revue canadienne de biochimie et biologie cellulaire 63(12) (1985) 953-968
The specific polysaccharide of Streptococcus pneumoniae type 11F (American type 11) is composed of 2-acetamido-2-deoxy-D-glucose (one part), D-glucose (one part), D-galactose (two parts), ribitol (one part), phosphate (one part), and O-acetyl (two parts). Hydrolysis, dephosphorylation, periodate oxidation, methylation, optical rotation, and 1H and 13C nuclear magnetic resonance studies showed that the polysaccharide is an unbranched linear polymer of a ribitol-phosphate substituted repeating tetrasaccharide unit having the structure: (Formula: see text). The specific capsular polysaccharides of S. pneumoniae type 11B and 11C (American types 76 and 53) were found to have the same tetrasaccharide repeating unit as the 11F polysaccharide, but differed from it in their mode of O-acetylation and the replacement of the ribitol phosphate by glycerol phosphate in the 11C specific polysaccharide.
NCBI PubMed ID: 4075231Publication DOI: 10.1139/o85-118Journal NLM ID: 8302763Publisher: Ottawa: National Research Council Of Canada
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario K1A OR6 Canada, Merck Sharp & Dohme Research Laboratories, West Point, PA, U.S.A. 19486
Methods: gel filtration, 13C NMR, 1H NMR, methylation, GLC-MS, sugar analysis, dephosphorylation, TLC, GLC, paper chromatography, de-O-acetylation, ion-exchange chromatography, immunodiffusion assays, periodate oxidation, optical rotation measurement
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