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1. Compound ID: 32
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b-D-Galf-(1-4)-+
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-6)-a-D-Glcp-(1-6)-b-D-Glcp-(1-3)-b-D-Galf-(1-3)-b-D-Glcp-(1-3)-a-D-GlcpNAc-(1-P- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_136095,IEDB_137340,IEDB_137472,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_150077,IEDB_151531,IEDB_190606,IEDB_241118,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 11
Beynon LM, Richards JC, Perry MB "Identification of the common antigenic determinant shared by Streptococcus pneumoniae serotypes 35A and 20 capsular polysaccharides - Structural analysis of the Streptococcus pneumoniae serotype 35A capsular polysaccharide" -
European Journal of Biochemistry 250(1) (1997) 163-167
The specific polysaccharide antigen of Streptococcus pneumoniae serotype 35A was shown, by a combination of one- and two-dimensional NMR methods and chemical analyses, to be a high-molecular-mass polymer composed of D-galactose, D-glucose, mannitol, and phosphate (3:1:1:1). The pentasaccharide repeating unit is polymerized through phosphate diester linkages to give the structure, [formula in text] O-Acetyl substituents are present at positions 5 and 6 of the 3)-β-D-Galf residue and at position 2 of the 6)-β-D-Galf residue. The capsular polysaccharides of S. pneumoniae serotypes 20 and 35A both contain the disaccharide unit →3)-β-D-Galf-(1→3)-β-D-Glcp-(1→ which is the probable structural determinant responsible for the serological cross reactivity of the two polysaccharides
structure, Streptococcus pneumoniae, antigenic determinant, capsular polysaccharides
NCBI PubMed ID: 9432005Publication DOI: 10.1111/j.1432-1033.1997.00163.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa ON
Methods: FAB-MS, GC-MS, GC-EI-MS, NMR, HF solvolysis, de-O-acylation
- Article ID: 1347
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, Bacterial polysaccharide, polysaccharides, 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: 1908
Richards JC, Perry MB, Carlo DJ "The specific capsular polysaccharide of Streptococcus pneumoniae type 20" -
Canadian Journal of Biochemistry and Cell Biology = Revue canadienne de biochimie et biologie cellulaire 61 (1983) 178-190
The specific capsular polysaccharide produced by Streptococcus pneumoniae type 20 is composed of D-glucose (three parts), D-galactose (two parts), 2-acetarnido-2-deoxy-D-glucose (one part), phosphate (one part), and O-acetyl (approximately two parts). Methylation, periodate oxidation, optical rotation, nuclear magnetic resonance, partial and enzymic hydrolyses, and chromatographic studies showed that the polysaccharide is a high molecular weight polymer of partially O-acetylated hexasaccharide repeating units linked by monophosphate, having the structure indicated below: [formula: see text].
NCBI PubMed ID: 6850414Publication DOI: 10.1139/o83-026Journal NLM ID: 8302763Publisher: Ottawa: National Research Council Of Canada
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario K1A OR6 Canada
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, gel filtration, partial acid hydrolysis, sugar analysis, GLC, paper chromatography, GPC, ion-exchange chromatography, optical rotation measurement
- Article ID: 4283
Calix JJ, Porambo RJ, Brady AM, Larson TR, Yother J, Abeygunwardana C, Nahm MH "Biochemical, genetic and serological characterization of two capsule subtypes among Streptococcus pneumoniae serotype 20 strains: discovery of a new pneumococcal serotype" -
Journal of Biological Chemistry 287(33) (2012) 27885-27894
The bacterial pathogen Streptococcus pneumoniae expresses one of over 90 structurally distinct polysaccharide (PS) capsule serotypes. Prior PS structural analyses of the vaccine-associated serotype 20 do not agree with reports describing the genes that mediate capsule synthesis. Furthermore, using immunized human sera-based assays serological differences were recently noted among strains typed as serotype 20. We examined the capsule structures of two serologically dissimilar serotype 20 strains, 20α and 20β, by extensive biochemical analysis. 20α PS was composed of the previously described serotype 20 hexasaccharide repeat unit, while the 20β PS was composed of a novel heptasaccharide repeat unit containing an extra branching α-glucose residue. Genetic analysis of the subtypes revealed that 20α may have arisen from a 20β progenitor following loss-of-function mutation to the glycosyltransferase gene whaF. Conventional serotyping methods using rabbit polyclonal or mouse monoclonal antibodies were unable to distinguish the subtypes. However, genetic analysis of multiple 'serotype 20' clinical isolates revealed that all strains contain the 20β genotype. We propose naming the bacteria that express the previously described 20α capsule structure 20A, and bacteria that express the novel 20β capsule structure 20B, a new pneumococcal serotype.
Streptococcus pneumoniae, monoclonal antibodies, capsule, serotyping, CPS, genetic characterization
NCBI PubMed ID: 22736767Publication DOI: 10.1074/jbc.M112.380451Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: nahm@uab.edu
Institutions: Department of Microbiology, University of Alabama at Birmingham, Birmingham, Alabama 35294, USA
Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, GC-MS, sugar analysis, de-O-acetylation, serological methods, genetic methods, biochemical methods
- Article ID: 4836
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: 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: 13C NMR, 1H NMR, gel filtration, sugar analysis, MS/MS, MS, dialysis, SEC-HPLC, ultrafiltration, mild deamination
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2. Compound ID: 737
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a-Kdop-(2-4)-+
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P-6)-+ | P-4)-+
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a-D-3dlyxHepp-ulosaric-(2-6)-b-D-Glcp-(1-4)-a-D-3dlyxHepp-ulosaric-(2-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-b-D-Glcp-(1-4)-a-D-Glcp-(1-5)-a-Kop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_135394,IEDB_135608,IEDB_135609,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_151531,IEDB_241118,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 196
Vinogradov EV, Müller-Loennies S, Petersen BO, Meshkov S, Thomas-Oates JE, Holst O, Brade H "Structural investigation of the lipopolysaccharide from Acinetobacter haemolyticus strain NCTC 10305 (ATCC 17906, DNA group 4)" -
European Journal of Biochemistry 247(1) (1997) 82-90
The structure of the lipopolysaccharide (LPS) from Acinetobacer haemolyticus strain NCTC 10305 (DNA group 4) was elucidated by means of analytical chemistry, NMR spectroscopy and fast-atom-bombardment mass spectrometry. Several oligosaccharides were obtained after deacylation or successive de-O-acylation, dephosphorylation, reduction, and de-N-acylation of LPS. In the major fraction of the LPS, the core is attached to the lipid A through D-glycero-D-talo-2-octulopyranosonic acid (Ko), whereas in a minor fraction (<20%) Ko is replaced by 3-deoxy-D-manno-octulopyranosonic acid (Kdo). The structures of the phosphorylated carbohydrate backbones of these LPS fractions are [see formula in text] with Dha = 3-deoxy-D-lyxo-2-heptulosaric acid, Sug = sugar and is Ko in a major fraction and Kdo in a minor fraction. All sugar residues have the D-configuration and are present in the pyranose form. Mass spectrometry of de-O-acylated LPS revealed the presence of and additional hexose residue in minor amounts, the position and nature of which could not be identified.
Lipopolysaccharide, NMR, structure, Acinetobacter, core-lipid A region
NCBI PubMed ID: 9249012Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark, Division of Medical and Microbiology, Center for Medicine and Biosciences, Research Center Borstel, Germany, Insitute of Chemical Physics, Russian Academy of Sciences, Moscow, Russia, Department of Mass Spectrometry, Bijvoet Center for Biomolecular Research, Universiteit Utrecht, The Netherlands
Methods: NMR-2D, FAB-MS, NMR, analytical methods
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3. Compound ID: 738
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a-Kdop-(2-4)-+
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P-6)-+ | P-4)-+
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a-D-3dlyxHepp-ulosaric-(2-6)-b-D-Glcp-(1-4)-a-D-3dlyxHepp-ulosaric-(2-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-b-D-Glcp-(1-4)-a-D-Glcp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_135394,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_150908,IEDB_151531,IEDB_241118,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 196
Vinogradov EV, Müller-Loennies S, Petersen BO, Meshkov S, Thomas-Oates JE, Holst O, Brade H "Structural investigation of the lipopolysaccharide from Acinetobacter haemolyticus strain NCTC 10305 (ATCC 17906, DNA group 4)" -
European Journal of Biochemistry 247(1) (1997) 82-90
The structure of the lipopolysaccharide (LPS) from Acinetobacer haemolyticus strain NCTC 10305 (DNA group 4) was elucidated by means of analytical chemistry, NMR spectroscopy and fast-atom-bombardment mass spectrometry. Several oligosaccharides were obtained after deacylation or successive de-O-acylation, dephosphorylation, reduction, and de-N-acylation of LPS. In the major fraction of the LPS, the core is attached to the lipid A through D-glycero-D-talo-2-octulopyranosonic acid (Ko), whereas in a minor fraction (<20%) Ko is replaced by 3-deoxy-D-manno-octulopyranosonic acid (Kdo). The structures of the phosphorylated carbohydrate backbones of these LPS fractions are [see formula in text] with Dha = 3-deoxy-D-lyxo-2-heptulosaric acid, Sug = sugar and is Ko in a major fraction and Kdo in a minor fraction. All sugar residues have the D-configuration and are present in the pyranose form. Mass spectrometry of de-O-acylated LPS revealed the presence of and additional hexose residue in minor amounts, the position and nature of which could not be identified.
Lipopolysaccharide, NMR, structure, Acinetobacter, core-lipid A region
NCBI PubMed ID: 9249012Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark, Division of Medical and Microbiology, Center for Medicine and Biosciences, Research Center Borstel, Germany, Insitute of Chemical Physics, Russian Academy of Sciences, Moscow, Russia, Department of Mass Spectrometry, Bijvoet Center for Biomolecular Research, Universiteit Utrecht, The Netherlands
Methods: NMR-2D, FAB-MS, NMR, analytical methods
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4. Compound ID: 742
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a-Kdop-(2-4)-+
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P-6)-+ | P-4)-+
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a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-b-D-Glcp-(1-4)-a-D-Glcp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_135394,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_150908,IEDB_151531,IEDB_241118,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 196
Vinogradov EV, Müller-Loennies S, Petersen BO, Meshkov S, Thomas-Oates JE, Holst O, Brade H "Structural investigation of the lipopolysaccharide from Acinetobacter haemolyticus strain NCTC 10305 (ATCC 17906, DNA group 4)" -
European Journal of Biochemistry 247(1) (1997) 82-90
The structure of the lipopolysaccharide (LPS) from Acinetobacer haemolyticus strain NCTC 10305 (DNA group 4) was elucidated by means of analytical chemistry, NMR spectroscopy and fast-atom-bombardment mass spectrometry. Several oligosaccharides were obtained after deacylation or successive de-O-acylation, dephosphorylation, reduction, and de-N-acylation of LPS. In the major fraction of the LPS, the core is attached to the lipid A through D-glycero-D-talo-2-octulopyranosonic acid (Ko), whereas in a minor fraction (<20%) Ko is replaced by 3-deoxy-D-manno-octulopyranosonic acid (Kdo). The structures of the phosphorylated carbohydrate backbones of these LPS fractions are [see formula in text] with Dha = 3-deoxy-D-lyxo-2-heptulosaric acid, Sug = sugar and is Ko in a major fraction and Kdo in a minor fraction. All sugar residues have the D-configuration and are present in the pyranose form. Mass spectrometry of de-O-acylated LPS revealed the presence of and additional hexose residue in minor amounts, the position and nature of which could not be identified.
Lipopolysaccharide, NMR, structure, Acinetobacter, core-lipid A region
NCBI PubMed ID: 9249012Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark, Division of Medical and Microbiology, Center for Medicine and Biosciences, Research Center Borstel, Germany, Insitute of Chemical Physics, Russian Academy of Sciences, Moscow, Russia, Department of Mass Spectrometry, Bijvoet Center for Biomolecular Research, Universiteit Utrecht, The Netherlands
Methods: NMR-2D, FAB-MS, NMR, analytical methods
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5. Compound ID: 743
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a-Kdop-(2-4)-+
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P-6)-+ | P-4)-+
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a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-b-D-Glcp-(1-4)-a-D-Glcp-(1-5)-a-Kop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_135394,IEDB_135608,IEDB_135609,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_151531,IEDB_241118,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 196
Vinogradov EV, Müller-Loennies S, Petersen BO, Meshkov S, Thomas-Oates JE, Holst O, Brade H "Structural investigation of the lipopolysaccharide from Acinetobacter haemolyticus strain NCTC 10305 (ATCC 17906, DNA group 4)" -
European Journal of Biochemistry 247(1) (1997) 82-90
The structure of the lipopolysaccharide (LPS) from Acinetobacer haemolyticus strain NCTC 10305 (DNA group 4) was elucidated by means of analytical chemistry, NMR spectroscopy and fast-atom-bombardment mass spectrometry. Several oligosaccharides were obtained after deacylation or successive de-O-acylation, dephosphorylation, reduction, and de-N-acylation of LPS. In the major fraction of the LPS, the core is attached to the lipid A through D-glycero-D-talo-2-octulopyranosonic acid (Ko), whereas in a minor fraction (<20%) Ko is replaced by 3-deoxy-D-manno-octulopyranosonic acid (Kdo). The structures of the phosphorylated carbohydrate backbones of these LPS fractions are [see formula in text] with Dha = 3-deoxy-D-lyxo-2-heptulosaric acid, Sug = sugar and is Ko in a major fraction and Kdo in a minor fraction. All sugar residues have the D-configuration and are present in the pyranose form. Mass spectrometry of de-O-acylated LPS revealed the presence of and additional hexose residue in minor amounts, the position and nature of which could not be identified.
Lipopolysaccharide, NMR, structure, Acinetobacter, core-lipid A region
NCBI PubMed ID: 9249012Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Chemistry, Carlsberg Laboratory, Copenhagen, Denmark, Division of Medical and Microbiology, Center for Medicine and Biosciences, Research Center Borstel, Germany, Insitute of Chemical Physics, Russian Academy of Sciences, Moscow, Russia, Department of Mass Spectrometry, Bijvoet Center for Biomolecular Research, Universiteit Utrecht, The Netherlands
Methods: NMR-2D, FAB-MS, NMR, analytical methods
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6. Compound ID: 805
Structure type: polymer chemical repeating unit
Compound class: CPS, teichoic acid
Contained glycoepitopes: IEDB_130695,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_232584,IEDB_241118,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 214
Wang Y, Huebner J, Tzianabos AO, Martirosian G, Kasper DL, Pier GB "Structure of an antigenic teichoic acid shared by clinical isolates of Enterococcus faecalis and vancomycin-resistant Enterococcus faecium" -
Carbohydrate Research 316(1-4) (1999) 155-160
A shared antigenic teichoic acid, previously found to be a surface capsule-like polysaccharide, was isolated from clinical isolates of Enterococcus faecalis and vancomycin-resistant E. faecium. It was composed of glucose, glycerol, and phosphate as determined by chemical and GC-MS analysis. The repeating-unit structure was elucidated by a series of 1H, 13C, and 31P NMR spectroscopy to be the following: [see formula in text]
structure, clinical, isolate, polysaccharide, acid, antigenic, Enterococcus, teichoic acid
NCBI PubMed ID: 10420594Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: ywang@channing.harvard.edu
Institutions: Channing Laboratory, Department of Medicine, Brigham and Women 's Hospital, Harvard Medical School, 181 Longwood Avenue, Boston, MA 02115- 5804, USA, Department of Microbiology and Molecular Genetics, Harvard Medical School, Boston, MA 02115, USA
Methods: GC-MS, chemical analysis
- Article ID: 823
Huebner J, Wang Y, Krueger WA, Madoff LC, Martirosian G, Boisot S, Goldmann DA, Kasper DL, Tzianabos AO, Pier GB "Isolation and chemical characterization of a capsular polysaccharide antigen shared by clinical isolates of Enterococcus faecalis and vancomycin-resistant Enterococcus faecium" -
Infection and Immunity 67(3) (1999) 1213-1219
Enterococci are a common cause of serious infections, especially in newborns, severely immunocompromised patients, and patients requiring intensive care. To characterize enterococcal surface antigens that are targets of opsonic antibodies, rabbits were immunized with various gentamicin-killed Enterococcus faecalis strains, and immune sera were tested in an opsonophagocytic assay against a selection of clinical isolates. Serum raised against one strain killed the homologous strain (12030) at a dilution of 1:5, 120 and mediated opsonic killing of 33% of all strains tested. In addition, this serum killed two (28%) of seven vancomycin-resistant Enterococcus faecium strains. Adsorption of sera with the homologous strain eliminated killing activity. The adsorbing antigens were resistant to treatment with proteinase K and to boiling for 1 h, but were susceptible to treatment with sodium periodate, indicating that the antigen inducing opsonic activity is a polysaccharide. Antibodies in immune rabbit sera reacted with a capsule-like structure visualized by electron microscopy both on the homologous E. faecalis strain and on a vancomycin-resistant E. faecium strain. The capsular polysaccharides from E. faecalis 12030 and E. faecium 838970 were purified, and chemical and structural analyses indicated they were identical glycerol teichoic acid-like molecules with a carbohydrate backbone structure of 6-a-D-glucose-1-2 glycerol-3-PO4 with substitution on carbon 2 of the glucose with an a-2-l-D-glucose residue. The purified antigen adsorbed opsonic killing activity from immune rabbit sera and elicited high titers of antibodies (when used to immunize rabbits) that both mediated opsonic killing of bacteria and bound to a capsule-like structure visualized by electron microscopy. These results indicate that approximately one-third of a sample of 15 E. faecalis strains and 7 vancomycin-resistant E. faecium strains possess shared capsular polysaccharides that are targets of opsonophagocytic antibodies and therefore are potential vaccine candidates.
antigen, clinical, isolate, capsular, characterization, polysaccharide, capsular polysaccharide, chemical, isolation, Enterococcus, polysaccharide antigen
NCBI PubMed ID: 10024563Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: gpier@channing.harvard.edu
Institutions: Channing Laboratory, Department of Medicine, Brigham and Women's Hospital, and Department of Medicine,Children's Hospital, Harvard Medical School, Boston, Massachusetts 02115-5899
Methods: GC-MS, NMR
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7. Compound ID: 1039
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Cho-(1--P--6)--a-D-Glcp-(1-3)-+ b-D-Glcp-(1-4)-+
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b-D-Galp-(1-4)-b-D-Glcp-(1-3)-L-gro-a-D-manHepp2Ac-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Sug
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EtN-(1--P--6)--+
Sug = anhKdo-ol |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_120354,IEDB_123890,IEDB_136044,IEDB_137472,IEDB_137779,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140624,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_190606,IEDB_2189047,IEDB_241118,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 306
Li J, Bauer SH, Mansson M, Moxon ER, Richards JC, Schweda E "Glycine is a common substituent of the inner core in Haemophilus influenzae lipopolysaccharide" -
Glycobiology 11(12) (2001) 1009-1015
A survey of both typeable and nontypeable strains of Haemophilus influenzae indicated that they contain glycine (Gly) in theirlipopolysaccharide (LPS). Significant amounts (30-250 pmol Gly/microg LPS) were determined by high-performanceanion-exchange chromatography using pulsed amperometric detection after treatment of the LPS with mild alkali.Oligosaccharides obtained from LPS after mild acid hydrolysis and gel filtration chromatography were investigated byelectrospray ionization mass spectrometry (ESI-MS) and capillary electrophoresis (CE) ESI-MS. In all cases, molecular ionscorresponding to the major glycoforms were identified and were accompanied by ions differing by 57 Da, thus indicating thepresence of glycine. The position of glycine in these glycoforms was determined by CE-ESI-MS/MS analyses. It was foundthat, depending on strain, glycine can substitute each of the heptoses of the inner-core element,L-α-D-Hepp-(1→2)-[PEtn→6]-L-α-D-Hepp-(1→3)-L-α-D-Hepp-(1→5)-α-Kdo of H. influenzae LPS aswell as Kdo. In some strains, mixtures of monosubstituted Gly-containing glycoforms having different substitution patternswere identified.
Lipopolysaccharide, Haemophilus, Haemophilus influenzae, common, core, inner core, glycine, CE-ESI-MS/MS
NCBI PubMed ID: 11805073Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada KlA OR6, Clinical Research Centre, Karolinska Institute and University College of South Stockholm, NOVUM, S-141 86 Huddinge, Sweden, Molecular Infectious Diseases Group, University of Oxford Department of Pediatrics, Weatherall Institute of Molecular Medicine, John Radcliffe Hospital, Headmgton, Oxford 0X3 9DS. UK
Methods: ESI-MS, mild acid hydrolysis, HPAEC, CE-ESI-MS/MS
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8. Compound ID: 1052
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b-D-Galf-(1-4)-+
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-6)-a-D-Glcp-(1-6)-b-D-Glcp-(1-3)-b-D-Galf5Ac6Ac-(1-3)-b-D-Glcp-(1-3)-a-D-GlcpNAc-(1-P- |
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Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl phosphate)
Compound class: CPS
Contained glycoepitopes: IEDB_136095,IEDB_137340,IEDB_137472,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_150077,IEDB_151531,IEDB_190606,IEDB_241118,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 301
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: 3365
Nikolaev AV, Botvinko IV, Ross AJ "Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis" -
Carbohydrate Research 342(3-4) (2007) 297-344
An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).
synthesis, structure, polysaccharides, Phosphoglycans, Anomeric phosphodiesters
NCBI PubMed ID: 17092493Publication DOI: 10.1016/j.carres.2006.10.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: a.v.nikolaev@dundee.ac.uk
Institutions: College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK.
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9. Compound ID: 1413
|
EtN-(1---P---P---6)-+
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Cho-(1--P--6)--a-D-Glcp-(1-3)-+ b-D-Glcp-(1-4)-+ |
| | |
Cho-(1--P--6)--b-D-Galp4Ac-(1-2)-L-gro-a-D-manHepp3Ac-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
|
EtN-(1--P--6)--+ |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_120354,IEDB_123890,IEDB_130650,IEDB_136044,IEDB_137472,IEDB_137779,IEDB_138949,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140624,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_148488,IEDB_190606,IEDB_2189047,IEDB_241118,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: 443
Landerholm MK, Li J, Richards JC, Hood DW, Moxon ER, Schweda EK "Characterization of novel structural features in the lipopolysaccharide of nondisease associated nontypeable Haemophilus influenzae" -
European Journal of Biochemistry 271(5) (2004) 941-953
Nontypeable Haemophilus influenzae (NTHi) is a common commensal of the human upper respiratory tract and is associated with otitis media in children. The structures of the oligosaccharide portions of NTHi lipopolysaccharide (LPS) from several otitis media isolates are now well characterized but it is not known whether there are structural differences in LPS from colonizing, nondisease associated strains. Structural analysis of LPS from nondisease associated NTHi strains 11 and 16 has been achieved by the application of high-field NMR techniques, ESI-MS, ESI-MSn, capillary electrophoresis coupled to ESI-MS, composition and linkage analyses on O-deacylated LPS and core oligosaccharide material. This is the first study to report structural details on LPS from strains taken from the nasopharynx from healthy individuals. Both strains express identical structures and contain the common element of H. influenzae LPS, L-α-D-Hepp-(1→2)-[PEtn→6]-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp-(1→5)-[PPEtn→4]-α-Kdop-(2→6)-lipid A, in which each heptose is elongated by a single hexose residue with no further oligosaccharide extensions. In the major Hex3 glycoform, the terminal Hepp residue (HepIII) is substituted at the O-2 position by a β-D-Galp residue and the central Hepp residue (HepII) is substituted at O-3 by a α-D-Glcp residue. Notably, the strains express two phosphocholine (PCho) substituents, one at the O-6 position of α-D-Glcp and the other at the O-6 position of β-D-Galp. Major acetylation sites were identified at O-4 of Gal and O-3 of HepIII. Additionally, both strains express glycine, and strain 11 also expresses detectable amounts of N-acetylneuraminic acid
Lipopolysaccharide, NMR, Haemophilus influenzae, ESI-MS, carriage
NCBI PubMed ID: 15009206Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: elke.schweda@kfc.ki.se
Institutions: Clinical Research Centre, Karolinska Institutet and University College of South Stockholm, NOVUM, Huddinge, Sweden Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada Molecular Infectious Diseases Group, University of Oxford, Department of Paediatrics, Weatherall Institute of Molecular Medicine, John Radcliffe Hospital, Oxford, UK
Methods: NMR-2D, NMR, ESI-MS, de-O-acetylation
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10. Compound ID: 1636
|
b-D-Galf-(1-4)-+
|
-6)-a-D-Glcp-(1-6)-b-D-Glcp-(1-3)-b-D-Galf-(1-3)-b-D-Glcp-(1-3)-a-D-GlcpNAc-(1-P- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_136095,IEDB_137340,IEDB_137472,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_150077,IEDB_151531,IEDB_190606,IEDB_241118,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 507
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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11. Compound ID: 2631
Structure type: monomer
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_241118,IEDB_983931,SB_192,SB_61
The structure is contained in the following publication(s):
- Article ID: 897
Kondakova AN, Senchenkova SN, Gremyakov AI, Shashkov AS, Knirel YA, Fudala R, Kaca W "Structure of the O-specific polysaccharide of Proteus mirabilis O38 containing 2-acetamidoethyl phosphate and N-linked D-aspartic acid" -
Carbohydrate Research 338(22) (2003) 2387-2392
The O-antigen of Proteus mirabilis O38 was found to be unique among bacterial polysaccharides and to have the following structure: [carbohydrate structure in text] where D-Qui4N(Ac-D-Asp) is 4-(N-acetyl-D-aspart-4-ylamino)-4,6-dideoxy-D-glucose and AcEtnP is 2-acetamidoethyl phosphate. Neither of these entities have been hitherto found in natural polysaccharides. Structural studies were performed using 1D and 2D NMR spectroscopy, including experiments run in an H2O/D2O mixture to reveal correlations for NH protons. In addition, dephosphorylation, carboxyl reduction and selective cleavages were applied. Solvolysis of the polysaccharide with anhydrous HF gave an α-D-GlcNAc-(1→3)-D-Qui4N(Ac-D-Asp) disaccharide. Solvolysis with trifluoromethanesulfonic (triflic) acid afforded D-GlcNAc6(AcEtnP), thus showing the suitability of this reagent for the preparation of phosphorylated sugar derivatives.
Lipopolysaccharide, Proteus mirabilis, aspartic acid, O-Polysaccharide structure, serogroup classification
NCBI PubMed ID: 14572723Publication DOI: 10.1016/j.carres.2003.07.001Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology and Immunology, University of Lodz, 90-237 Lodz, Poland, Center of Microbiology and Virology, Polish Academy of Sciences, 93-232 Lodz, Poland
Methods: NMR, HF solvolysis, dephosphorylation, ESI-MS, carboxyl reduction, triflic acid solvolysis
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12. Compound ID: 2721
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a-L-Fucp-(1-4)-+
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-3)-a-D-Glcp-(1--P--6)--a-D-Glcp-(1-2)-b-D-Glcp-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136045,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144998,IEDB_144999,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_241118,IEDB_983931,SB_192,SB_86
The structure is contained in the following publication(s):
- Article ID: 942
Linnerborg M, Weintraub A, Widmalm G "Structural studies of the O-antigen polysaccharide from the enteroinvasive Escherichia coli O173" -
Carbohydrate Research 320(3-4) (1999) 200-208
The structure of the O-antigen polysaccharide (PS) from Escherichia coli O173 has been investigated. Sugar and methylation analyses, electrospray ionisation mass spectrometry together with 1H, 31P and 13C NMR spectroscopy were the main methods used. The structure of the pentasaccharide repeating unit of the PS was found to be: [see structure in text]. By treatment with 48% HF the phosphoric diester linkage was cleaved together with the glycosidic linkage of the fucosyl group, rendering a tetrasaccharide with the structure: a-D-Glcp-(1→2)-b-D-Glcp-(1→3)-b-D-GlcpNAc-(1→3)-D-Glc.
structural, polysaccharide, O-antigen, O antigen, Escherichia, Escherichia coli, structural studies
NCBI PubMed ID: 10573858Publication DOI: 10.1016/S0008-6215(99)00142-1Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: G. Widmalm
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S- 106 91 Stockholm, Sweden, Karolinska Institute, Department of Immunology, Microbiology, Pathology and Infectious Diseases, Division of Clinical and Oral Bacteriology, Huddinge University Hospital, S- 141 86 Huddinge, Sweden
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, ESI-MS
- Article ID: 1548
Olsson U, Lycknert K, Stenutz R, Weintraub A, Widmalm G "Structural analysis of the O-antigen polysaccharide from Escherichia coli O152" -
Carbohydrate Research 340(1) (2005) 167-171
The structure of the O-antigen polysaccharide (PS) from Escherichia coli O152 has been determined. Component analysis together with (1)H, (13)C and (31)P NMR spectroscopy were used to elucidate the structure. Inter-residue correlations were determined by (1)H,(31)P COSY, (1)H,(1)H NOESY and (1)H,(13)C heteronuclear multiple-bond correlation experiments. The PS is composed of pentasaccharide repeating units with the following structure: The structure is similar to that of the O-antigen polysaccharide from E. coli O173. The cross-reactivity between E. coli O152 and E. coli O3 may be explained by structural similarities in the branching region of their O-antigen polysaccharides
NMR, structure, chemistry, correlation, structural, polysaccharide, O-antigen, repeating unit, analysis, O antigen, Escherichia, Escherichia coli, NMR spectroscopy, structural analysis, polysaccharides, region, spectroscopy, pentasaccharide, component, similarity, cross-reactivity, crossreactivity, organic, NOESY, COSY, heteronuclear
NCBI PubMed ID: 15620681Publication DOI: 10.1016/j.carres.2004.11.008Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, Karolinska Institute, Department of Laboratory Medicine, Division of Clinical Bacteriology, F-82 Karolinska University Hospital, Huddinge Stockholm, Sweden
Methods: NMR, composition analysis
- Article ID: 3197
Stenutz R, Weintraub A, Widmalm G "The structures of Escherichia coli O-polysaccharide antigens" -
FEMS Microbiology Reviews 30(3) (2006) 382-403
Escherichia coli is usually a non-pathogenic member of the human colonic flora. However, certain strains have acquired virulence factors and may cause a variety of infections in humans and in animals. There are three clinical syndromes caused by E. coli: (i) sepsis/meningitis; (ii) urinary tract infection and (iii) diarrhoea. Furthermore the E. coli causing diarrhoea is divided into different 'pathotypes' depending on the type of disease, i.e. (i) enterotoxigenic; (ii) enteropathogenic; (iii) enteroinvasive; (iv) enterohaemorrhagic; (v) enteroaggregative and (vi) diffusely adherent. The serotyping of E. coli based on the somatic (O), flagellar (H) and capsular polysaccharide antigens (K) is used in epidemiology. The different antigens may be unique for a particular serogroup or antigenic determinants may be shared, resulting in cross-reactions with other serogroups of E. coli or even with other members of the family Enterobacteriacea. To establish the uniqueness of a particular serogroup or to identify the presence of common epitopes, a database of the structures of O-antigenic polysaccharides has been created. The E. coli database (ECODAB) contains structures, nuclear magnetic resonance chemical shifts and to some extent cross-reactivity relationships. All fields are searchable. A ranking is produced based on similarity, which facilitates rapid identification of strains that are difficult to serotype (if known) based on classical agglutinating methods. In addition, results pertinent to the biosynthesis of the repeating units of O-antigens are discussed. The ECODAB is accessible to the scientific community at http://www.casper.organ.su.se/ECODAB/
NMR, structure, serotype, O-antigen, Enterobacteriacea, database
NCBI PubMed ID: 16594963Publication DOI: 10.1111/j.1574-6976.2006.00016.xJournal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: andrej.weintraub@ki.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
- Article ID: 3365
Nikolaev AV, Botvinko IV, Ross AJ "Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis" -
Carbohydrate Research 342(3-4) (2007) 297-344
An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).
synthesis, structure, polysaccharides, Phosphoglycans, Anomeric phosphodiesters
NCBI PubMed ID: 17092493Publication DOI: 10.1016/j.carres.2006.10.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: a.v.nikolaev@dundee.ac.uk
Institutions: College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK.
- Article ID: 5472
Liu B, Furevi A, Perepelov AV, Guo X, Cao H, Wang Q, Reeves PR, Knirel YA, Wang L, Widmalm G "Structure and genetics of Escherichia coli O antigens" -
FEMS Microbiology Reviews 44(6) (2020) 655-683
Escherichia coli includes clonal groups of both commensal and pathogenic strains, with some of the latter causing serious infectious diseases. O antigen variation is current standard in defining strains for taxonomy and epidemiology, providing the basis for many serotyping schemes for Gram-negative bacteria. This review covers the diversity in E. coli O antigen structures and gene clusters, and the genetic basis for the structural diversity. Of the 187 formally defined O antigens, six (O31, O47, O67, O72, O94 and O122) have since been removed and four (O14, O34, O89 and O144) strains do not produce any O antigen. Therefore, structures are presented for 176 of the 181 E. coli O antigens, some of which include subgroups. Most (93%) of these O antigens are synthesized via the Wzx/Wzy pathway, 11 via the ABC transporter pathway, with O20, O57 and O60 still uncharacterized due to failure to find their O antigen gene clusters. Biosynthetic pathways are given for 38 of the 49 sugars found in E. coli O antigens, and several pairs or groups of the E. coli antigens that have related structures show close relationships of the O antigen gene clusters within clades, thereby highlighting the genetic basis of the evolution of diversity.
structure, O antigen, Escherichia coli, gene cluster, serogroup, diversity
NCBI PubMed ID: 31778182Publication DOI: 10.1093/femsre/fuz028Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: G. Widmalm
; Lei Wang
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Tianjin Key Laboratory of Microbial Functional Genomics, Tianjin, China, The Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, Tianjin, China, School of Molecular and Microbial Bioscience (G08), University of Sydney, Sydney, Australia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, Department of Immunology, School of Basic Medical Sciences, Tianjin Medical University, Tianjin, China
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13. Compound ID: 2741
|
b-L-Rhap-(1-4)-+
|
-3)-a-D-GlcpNAc-(1--P--6)--a-D-Glcp-(1-2)-b-D-Glcp-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_150077,IEDB_151531,IEDB_225177,IEDB_241118,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 959
MacLean LL, Perry MB "Structural studies on the O-polysaccharide of the lipopolysaccharide produced by Citrobacter rodentium (ATCC51459)" -
European Journal of Biochemistry 268(22) (2001) 5740-5746
Citrobacter rodentium is the etiologic agent of transmissible murine colonic hyperplasia (TMCH) and is the only Citrobacter species known to possess virulence factors homologous to human enteropathogenic and enterohemorrhagic Escherichia coli. Members of this species are considered clonal and represent the only known attaching and effacing bacterial pathogen of mice and thus provides a useful animal model for studying the molecular basis of attaching and effacing pathology. The lipopolysaccharide (LPS) produced by C. rodentium has not been previously studied or its possible role as a virulence factor determined. The structure of the LPS has been undertaken as a first step in an investigation of its possible role in pathogenesis. The structure of C. rodentium (ATCC51459, prototype TMCH isolate, original biotype 4280, previously designated DBS 100) LPS was determined from composition and methylation analyses, mass spectrometry, and two-dimensional nuclear magnetic resonance spectroscopy. The antigenic O-polysaccharide was found to be a high molecular mass branched polymer of repeating pentasaccharide units composed of 2-acetamido-2-deoxy-D-glucose (D-GlcNAc), d-glucose (D-Glc), and L-rhamnose (L-Rha) in the molar ratio 2 : 2 : 1 linked through phosphate, and has the structure: [structure: see text]
Lipopolysaccharide, strain, structural, O-polysaccharide, O polysaccharide, structural studies, Citrobacter
NCBI PubMed ID: 11722558Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: malcolm.perry@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada K1A 0R6.
Methods: methylation, NMR-2D, NMR, MS, composition analysis
- Article ID: 1468
Knirel YA, Kocharova NA, Bystrova OV, Katzenellenbogen E, Gamian A "Structures and serology of the O-specific polysaccharides of bacteria of the genus Citrobacter" -
Archivum Immunologiae et Therapiae Experimentalis 50(6) (2002) 379-391
The review presents the structures of the O-specific polysaccharides (O-antigens) of the lipopolysaccharides isolated from over 25 Citrobacter strains, which represent different species and serogroups. The correlation between O-antigen structure and immunospecificity as well as numerous cross-reactions between Citrobacter and other enterobacterial species are discussed.
Lipopolysaccharide, structure, O-antigen, O-specific polysaccharide, serology, Citrobacter, immunospecificity
NCBI PubMed ID: 12546064Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 1548
Olsson U, Lycknert K, Stenutz R, Weintraub A, Widmalm G "Structural analysis of the O-antigen polysaccharide from Escherichia coli O152" -
Carbohydrate Research 340(1) (2005) 167-171
The structure of the O-antigen polysaccharide (PS) from Escherichia coli O152 has been determined. Component analysis together with (1)H, (13)C and (31)P NMR spectroscopy were used to elucidate the structure. Inter-residue correlations were determined by (1)H,(31)P COSY, (1)H,(1)H NOESY and (1)H,(13)C heteronuclear multiple-bond correlation experiments. The PS is composed of pentasaccharide repeating units with the following structure: The structure is similar to that of the O-antigen polysaccharide from E. coli O173. The cross-reactivity between E. coli O152 and E. coli O3 may be explained by structural similarities in the branching region of their O-antigen polysaccharides
NMR, structure, chemistry, correlation, structural, polysaccharide, O-antigen, repeating unit, analysis, O antigen, Escherichia, Escherichia coli, NMR spectroscopy, structural analysis, polysaccharides, region, spectroscopy, pentasaccharide, component, similarity, cross-reactivity, crossreactivity, organic, NOESY, COSY, heteronuclear
NCBI PubMed ID: 15620681Publication DOI: 10.1016/j.carres.2004.11.008Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, Karolinska Institute, Department of Laboratory Medicine, Division of Clinical Bacteriology, F-82 Karolinska University Hospital, Huddinge Stockholm, Sweden
Methods: NMR, composition analysis
- Article ID: 3197
Stenutz R, Weintraub A, Widmalm G "The structures of Escherichia coli O-polysaccharide antigens" -
FEMS Microbiology Reviews 30(3) (2006) 382-403
Escherichia coli is usually a non-pathogenic member of the human colonic flora. However, certain strains have acquired virulence factors and may cause a variety of infections in humans and in animals. There are three clinical syndromes caused by E. coli: (i) sepsis/meningitis; (ii) urinary tract infection and (iii) diarrhoea. Furthermore the E. coli causing diarrhoea is divided into different 'pathotypes' depending on the type of disease, i.e. (i) enterotoxigenic; (ii) enteropathogenic; (iii) enteroinvasive; (iv) enterohaemorrhagic; (v) enteroaggregative and (vi) diffusely adherent. The serotyping of E. coli based on the somatic (O), flagellar (H) and capsular polysaccharide antigens (K) is used in epidemiology. The different antigens may be unique for a particular serogroup or antigenic determinants may be shared, resulting in cross-reactions with other serogroups of E. coli or even with other members of the family Enterobacteriacea. To establish the uniqueness of a particular serogroup or to identify the presence of common epitopes, a database of the structures of O-antigenic polysaccharides has been created. The E. coli database (ECODAB) contains structures, nuclear magnetic resonance chemical shifts and to some extent cross-reactivity relationships. All fields are searchable. A ranking is produced based on similarity, which facilitates rapid identification of strains that are difficult to serotype (if known) based on classical agglutinating methods. In addition, results pertinent to the biosynthesis of the repeating units of O-antigens are discussed. The ECODAB is accessible to the scientific community at http://www.casper.organ.su.se/ECODAB/
NMR, structure, serotype, O-antigen, Enterobacteriacea, database
NCBI PubMed ID: 16594963Publication DOI: 10.1111/j.1574-6976.2006.00016.xJournal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: andrej.weintraub@ki.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
- Article ID: 3365
Nikolaev AV, Botvinko IV, Ross AJ "Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis" -
Carbohydrate Research 342(3-4) (2007) 297-344
An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).
synthesis, structure, polysaccharides, Phosphoglycans, Anomeric phosphodiesters
NCBI PubMed ID: 17092493Publication DOI: 10.1016/j.carres.2006.10.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: a.v.nikolaev@dundee.ac.uk
Institutions: College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK.
- Article ID: 3446
Brockhausen I, Hu B, Liu B, Lau K, Szarek WA, Wang L, Feng L "Characterization of two b-1,3-glucosyltransferases from Escherichia coli serotypes O56 and O152" -
Journal of Bacteriology 190(14) (2008) 4922-4932
The O antigens of outer membrane-bound lipopolysaccharides (LPS) in Gram-negative bacteria are oligosaccharides consisting of repeating units with various structures and antigenicities. The O56 and O152 antigens of Escherichia coli both contain a Glc-β 1-3-GlcNAc linkage within the repeating unit. We have cloned and identified the genes (wfaP in O56 and wfgD in O152) within the two O antigen gene clusters that encode glucosyltransferases involved in the synthesis of this linkage. A synthetic substrate analog of the natural acceptor substrate undecaprenol-pyrophosphate-lipid (GlcNAc-PP-PhU) was used as an acceptor and UDP-Glc as a donor substrate to demonstrate that both wfgD and wfaP encode glucosyltransferases. Enzyme products from both glucosyltransferases were isolated by HPLC and analyzed by NMR. The spectra showed the expected Glc-β 1-3-GlcNAc linkage in the products, confirming that both WfaP and WfgD are UDP-Glc: GlcNAc-pyrophosphate-lipid β-1,3-glucosyltransferases. Both WfaP and WfgD have a DxD sequence which is proposed to interact with phosphate groups of the nucleotide donor through the coordination of a metal cation, and a short hydrophobic sequence at the C terminus that may help to associate the enzymes with the inner membrane. We showed that the enzymes have similar properties and substrate recognition. They both require divalent cation (Mn(2+) or Mg(2+)) for activity, are deactivated by detergents, have a broad pH optimum, and require the pyrophosphate-sugar linkage in the acceptor substrate for full activity. Substrates lacking phosphate or pyrophosphate linked to GlcNAc were inactive. The length of the aliphatic chain of acceptor substrates also contributes to the activity.
O-antigen, gene cluster, Glucosyltransferases, enzymatic syntheses, Escherichia coli O56, Escherichia coli O152
NCBI PubMed ID: 18487334Publication DOI: 10.1128/JB.00160-08Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: fenglu63@nankai.edu.cn
Institutions: Department of Medicine, Department of Biochemistry, Queen's University, Kingston Ontario K7L 3N6, Canada, TEDA School of Biological Sciences and Biotechnology, Nankai University, Hongda Street, TEDA, Tianjin 300457, P.R.China, Tianjin Key Laboratory of Microbial Functional Genomics, P. R. China, Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, P. R. China, Department of Chemistry, Queen's University, Kingston Ontario K7L 3N6, Canada
Methods: 13C NMR, 1H NMR, genetic methods, biochemical methods, HPLC
- Article ID: 3506
Liu B, Knirel YA, Feng L, Perepelov AV, Senchenkova SN, Wang Q, Reeves P, Wang L "Structure and genetics of Shigella O antigens" -
FEMS Microbiology Reviews 32(4) (2008) 627-653
This review covers the O antigens of the 46 serotypes of Shigella, but those of most Shigella flexneri are variants of one basic structure, leaving 34 Shigella distinct O antigens to review, together with their gene clusters. Several of the structures and gene clusters are reported for the first time and this is the first such group for which structures and DNA sequences have been determined for all O antigens. Shigella strains are in effect Escherichia coli with a specific mode of pathogenicity, and 18 of the 34 O antigens are also found in traditional E. coli. Three are very similar to E. coli O antigens and 13 are unique to Shigella strains. The O antigen of Shigella sonnei is quite atypical for E. coli and is thought to have transferred from Plesiomonas. The other 12 O antigens unique to Shigella strains have structures that are typical of E. coli, but there are considerably more anomalies in their gene clusters, probably reflecting recent modification of the structures. Having the complete set of structures and genes opens the way for experimental studies on the role of this diversity in pathogenicity.
structure, O antigen, Shigella, O antigen gene cluster, O antigen diversity
NCBI PubMed ID: 18422615Publication DOI: 10.1111/j.1574-6976.2008.00114.xJournal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: wanglei@nankai.edu.cn
Institutions: TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China.
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, ESI-MS, serological methods, genetic methods, biochemical methods
- Article ID: 4329
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 5472
Liu B, Furevi A, Perepelov AV, Guo X, Cao H, Wang Q, Reeves PR, Knirel YA, Wang L, Widmalm G "Structure and genetics of Escherichia coli O antigens" -
FEMS Microbiology Reviews 44(6) (2020) 655-683
Escherichia coli includes clonal groups of both commensal and pathogenic strains, with some of the latter causing serious infectious diseases. O antigen variation is current standard in defining strains for taxonomy and epidemiology, providing the basis for many serotyping schemes for Gram-negative bacteria. This review covers the diversity in E. coli O antigen structures and gene clusters, and the genetic basis for the structural diversity. Of the 187 formally defined O antigens, six (O31, O47, O67, O72, O94 and O122) have since been removed and four (O14, O34, O89 and O144) strains do not produce any O antigen. Therefore, structures are presented for 176 of the 181 E. coli O antigens, some of which include subgroups. Most (93%) of these O antigens are synthesized via the Wzx/Wzy pathway, 11 via the ABC transporter pathway, with O20, O57 and O60 still uncharacterized due to failure to find their O antigen gene clusters. Biosynthetic pathways are given for 38 of the 49 sugars found in E. coli O antigens, and several pairs or groups of the E. coli antigens that have related structures show close relationships of the O antigen gene clusters within clades, thereby highlighting the genetic basis of the evolution of diversity.
structure, O antigen, Escherichia coli, gene cluster, serogroup, diversity
NCBI PubMed ID: 31778182Publication DOI: 10.1093/femsre/fuz028Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: G. Widmalm
; Lei Wang
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Tianjin Key Laboratory of Microbial Functional Genomics, Tianjin, China, The Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, Tianjin, China, School of Molecular and Microbial Bioscience (G08), University of Sydney, Sydney, Australia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, Department of Immunology, School of Basic Medical Sciences, Tianjin Medical University, Tianjin, China
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14. Compound ID: 2802
|
Cho-(1--P--6)--a-D-Glcp-(1-3)-+ b-D-Glcp-(1-4)-+ EtN-(1---P---P---4)-+
| | |
a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-3)-L-gro-a-D-manHepp2Ac-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
|
EtN-(1--P--6)--+ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide, LPS
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130679,IEDB_136044,IEDB_136794,IEDB_137472,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140624,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150933,IEDB_190606,IEDB_2189047,IEDB_241118,IEDB_983931,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_37,SB_39,SB_6,SB_68,SB_7,SB_76,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 980
Mansson M, Bauer SHJ, Hood DW, Richards JC, Moxon ER, Schweda EKH "A new structural type for Haemophilus influenzae lipopolysaccharide - Structural analysis of the lipopolysaccharide from nontypeable Haemophilus influenzae strain 486" -
European Journal of Biochemistry 268(7) (2001) 2148-2159
Structural elucidation of the sialylated lipopolysaccharide (LPS) of non-typeable Haemophilus influenzae (NTHi) strain 486 has been achieved by the application of high-field NMR techniques and ESI-MS along with composition and linkage analyses on O-deacylated LPS and oligosaccharide samples. It was found that the LPS contains the common element of H. influenzae, L-α-D-Hepp-(1→2)-[PEtn→6]-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp-(1→5)-[PPEtn→4]-α-Kdop-(2→6)-Lipid A, but instead of glycosyl substitution of the terminal heptose residue (HepIII) at the O2 position observed in other H. influenzae strains, HepIII is chain elongated at the O3 position by either lactose or sialyllactose (i.e. α-Neu5Ac-(2→3)-β-D-Galp-(1→4)-β-D-Glcp). The LPS is substituted by an O-acetyl group linked to the O2 position of HepIII and phosphocholine (PCho) which was located at the O6 position of a terminal α-D-Glcp residue attached to the central heptose, a molecular environment different from what has been reported earlier for PCho. In addition, minor substitution by O-linked glycine to the LPS was observed. By investigation of LPS from a lpsA mutant of NTHi strain 486, it was demonstrated that the lpsA gene product also is responsible for chain extension from HepIII in this strain. The involvement of lic1 in expression of PCho was established by investigation of a lic1 mutant of NTHi strain 486.
Lipopolysaccharide, Haemophilus, Haemophilus influenzae, strain, structural, analysis, type, structural analysis, Phosphocholine, sialic acid
NCBI PubMed ID: 11277939Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: elke.schweda@kfcmail.hs.sll.se
Institutions: University College of South Stockholm, Clinical Reseach Center,Huddinge,Sweden
Methods: NMR
- Article ID: 1460
Holst O "Chemical structure of the core region of lipopolysaccharides - an update" -
Trends in Glycoscience and Glycotechnology 14(76) (2002) 87-103
Lipopolysaccharides (LPS) are the endotoxins of Gram-negative bacteria and very well known for their immunological, pharmacological and pathophysiological effects displayed in eucaryotic cells and organisms. To date, much emphasis has been put on the elucidation of the chemical structures of LPS and on their relation, or that of substructures, to the various biological effects. The lipid part of LPS, the lipid A, was proven to represent the toxic principle of endotoxin. However, lipid A toxicity depends strongly on its structure, and is influenced by a second region of LPS, the core region, that is covalently linked to lipid A. Also, the core region possesses immunogenic properties. Therefore, complete structural analyses of the core region and the comparison of its structures with biological features of LPS are of high importance for a better understanding of LPS action, and one prerequesite for strategies aimed at the treatment of endotoxicosis. In the past, quite a number of structures of the core regions from various Gram-negative bacteria were published and summarized in several overviews. The present review adds to this knowledge those structures that were published between October 1998 and December 2001.
lipopolysaccharides, heptose, Kdo, chemical structure, core region, tructure
Publication DOI: 10.4052/tigg.14.87Journal NLM ID: 9425898Correspondence: oholst@fz-borstel.de
Institutions: Structural Biochemistry, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany
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15. Compound ID: 2803
|
Cho-(1--P--6)--a-D-Glcp-(1-3)-+ b-D-Glcp-(1-4)-+ EtN-(1---P---P---4)-+
| | |
a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-3)-L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/O-deacylated lipid A/
|
EtN-(1--P--6)--+ |
Show graphically |
Structure type: oligomer
Aglycon: O-deacylated lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130679,IEDB_136044,IEDB_136794,IEDB_137472,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140624,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150933,IEDB_190606,IEDB_2189047,IEDB_241118,IEDB_983931,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_37,SB_39,SB_6,SB_68,SB_7,SB_76,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 980
Mansson M, Bauer SHJ, Hood DW, Richards JC, Moxon ER, Schweda EKH "A new structural type for Haemophilus influenzae lipopolysaccharide - Structural analysis of the lipopolysaccharide from nontypeable Haemophilus influenzae strain 486" -
European Journal of Biochemistry 268(7) (2001) 2148-2159
Structural elucidation of the sialylated lipopolysaccharide (LPS) of non-typeable Haemophilus influenzae (NTHi) strain 486 has been achieved by the application of high-field NMR techniques and ESI-MS along with composition and linkage analyses on O-deacylated LPS and oligosaccharide samples. It was found that the LPS contains the common element of H. influenzae, L-α-D-Hepp-(1→2)-[PEtn→6]-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp-(1→5)-[PPEtn→4]-α-Kdop-(2→6)-Lipid A, but instead of glycosyl substitution of the terminal heptose residue (HepIII) at the O2 position observed in other H. influenzae strains, HepIII is chain elongated at the O3 position by either lactose or sialyllactose (i.e. α-Neu5Ac-(2→3)-β-D-Galp-(1→4)-β-D-Glcp). The LPS is substituted by an O-acetyl group linked to the O2 position of HepIII and phosphocholine (PCho) which was located at the O6 position of a terminal α-D-Glcp residue attached to the central heptose, a molecular environment different from what has been reported earlier for PCho. In addition, minor substitution by O-linked glycine to the LPS was observed. By investigation of LPS from a lpsA mutant of NTHi strain 486, it was demonstrated that the lpsA gene product also is responsible for chain extension from HepIII in this strain. The involvement of lic1 in expression of PCho was established by investigation of a lic1 mutant of NTHi strain 486.
Lipopolysaccharide, Haemophilus, Haemophilus influenzae, strain, structural, analysis, type, structural analysis, Phosphocholine, sialic acid
NCBI PubMed ID: 11277939Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: elke.schweda@kfcmail.hs.sll.se
Institutions: University College of South Stockholm, Clinical Reseach Center,Huddinge,Sweden
Methods: NMR
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