Found 65 structures.
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1. Compound ID: 1049
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D-Gro-(1--P--3)--+
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-4)-b-D-Glcp-(1-4)-b-D-Galp-(1-4)-a-D-Glcp-(1-?)-a-L-Rhap-(1-
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a-D-Glcp-(1-2)-+ |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130695,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153217,IEDB_158539,IEDB_190606,IEDB_225177,IEDB_885823,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: 300
Lee CH, Frasch CE "Quantification of bacterial polysaccharides by the purpald assay: Measurement of periodate-generated formaldehyde from glycol in the repeating unit" -
Analytical Biochemistry 296(1) (2001) 73-82
We have adapted the purpald assay for measurement of bacterial polysaccharides (PS) containing substituted and/or unsubstituted glycol (SG or UG) in residues such as glycerol, ribitol, arabinitol, furanosyl galactose, and sialyl. For the purpald assay of UG-containing PS, 50 microL of PS samples was consecutively reacted with 50 microL of 16 mM NaIO4 for 20 min, 50 microL of 136 mM purpald reagent in 2 N NaOH for 20 min, and 50 microL of 64 mM NaIO4 for 20 min in a 96-well tissue culture plate followed by a measurement of absorbance at 550 nm with a plate reader. For SG-containing PS, conversion of SG to UG with 25 micro;L of 0.3 N NaOH, 1 h at room temperature for de-O-acetylation followed by 25 microL of 0.6 M H2SO4, 1 h at 80 degrees C for acid hydrolysis of PS precedes the periodate treatment in the purpald assay. The concentration of the samples can be calculated from the sample absorbance and the reference standard curve constructed from the reference concentrations of the same PS (well-characterized) and their corresponding absorbance values assayed in the same plate. The purpald assay provides a tool in addition to the existing ones for the measurement of glycol-containing PS. Among the usefulness of this method are the determinations of the glycerol content in the phospho-glycerol-containing PS and the SG and UG contents and structural integrity in PS and conjugate vaccines.
repeating unit, bacterial polysaccharides, quantification
NCBI PubMed ID: 11520034Publication DOI: 10.1006/abio.2001.5230Journal NLM ID: 0370535Publisher: Academic Press
Institutions: Laboratory of Bacterial Polysaccharides, Division of Bacterial, Parasitic and Allergenic Products, OVRR, CBER, FDA, 8800 Rockville Pike, Bethesda, MD, USA
Methods: purpald assay measurement
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2. Compound ID: 1477
Structure type: oligomer
Compound class: O-linked glycoprotein
Contained glycoepitopes: IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_153217,IEDB_190606,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: 467
Schäffer C, Messner P "Surface-layer glycoproteins: an example for the diversity of bacterial glycosylation with promising impacts on nanobiotechnology" -
Glycobiology 14(8) (2004) 31R-42R
Bacterial cell surface layers, referred to simply as S-layers, have been described for all major phylogenetic groups of bacteria, which may indicate their pivotal role for a bacterium in its natural habitat. They have the unique ability to assemble into two-dimensional crystalline arrays that completely cover the bacterial cells. Glycosylation represents the most frequent modification of S-layer proteins. S-layer glycoproteins constitute a class of glycoconjugates first isolated in the mid-1970s, but S-layer glycoprotein research is still being regarded as an 'exotic field of glycobiology,' possibly because of its 'noneukaryotic' character. Extensive work over the past 30 years provided evidence of an enormous diversity of S-layer glycoproteins that have been created in nature over 3 billion years of prokaryotic evolution. These glycoconjugates are substantially different from eukaryotic glycoproteins, with regard to both composition and structure; nevertheless, some general structural concepts may be deduced. The awareness of the high application potential of S-layer glycoproteins, especially in combination with their intrinsic cell surface display feature, in the field of modern nanobiotechnology as a base for glycoengineering has recently led to the investigation of the S-layer protein glycosylation process at the molecular level, which has lagged behind the structural studies due to the lack of suitable molecular tools. From that work an even more interesting picture of this class of glycoconjugates is emerging. The availability of purified enzymes from S-layer glycan biosynthesis pathways exhibiting increased stabilities and/or rare sugar specificities in conjunction with preliminary genomic data on S-layer glycan biosynthesis clusters will pave the way for the rational design of S-layer neoglycoproteins.
LPS, bacterial glycosylation, genomic glycosylation loci, glycan diversity, glycoengineering, S-layer nanoglycobiology
NCBI PubMed ID: 15044388Publication DOI: 10.1093/glycob/cwh064Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: paul.messner@boka.ac.at
Institutions: Center for NanoBiotechnology, University of Applied Life Sciences and Natural Resources, Gregor-Mendel-Strasse 33, A-1180 Wien, Austria
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3. Compound ID: 1636
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D-Gro-(1--P--3)--+
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-4)-b-D-Glcp-(1-4)-b-D-Galp-(1-4)-a-D-Glcp-(1-3)-a-L-Rhap-(1-
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a-D-Glcp-(1-2)-+ |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130695,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153217,IEDB_158539,IEDB_190606,IEDB_225177,IEDB_885823,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: 506
Pujar NS, Huang NF, Daniels CL, Dieter L, Gayton MG, Lee AL "Base hydrolysis of phosphodiester bonds in pneumococcal polysaccharides" -
Biopolymers 75(1) (2004) 71-84
A comprehensive study of the base hydrolysis of all phosphodiester bond-containing capsular polysaccharides of the 23-valent pneumococcal vaccine is described here. Capsular polysaccharides from serotypes 6B, 10A, 17F, 19A, 19F, and 20 contain a phosphodiester bond that connects the repeating units in these polysaccharides (also referred to as backbone phosphodiester bonds), and polysaccharides from serotypes 11A, 15B, 18C, and 23F contain a phosphodiester bond that links a side chain to their repeating units. Molecular weight measurements of the polysaccharides, using high performance size exclusion chromatography with tandem multiangle laser light scattering and refractive index detection, was used to evaluate the kinetics of hydrolysis. The measurement of molecular weight provides a high degree of sensitivity in the case of small extents of reaction, thus allowing reliable measurements of the kinetics over short times. Pseudo-first-order rate constants for these polysaccharides were estimated using a simple model that accounts for the polydispersity of the starting sample. It was found that the relative order of backbone phosphodiester bond instability due to base hydrolysis was 19A > 10A > 19F > 6B > 17F, 20. Degradation of side-chain phosphodiester bonds was not observed, although the high degree of sensitivity in measurements is lost in this case, due to the low contribution of the side chains to the total polysaccharide molecular weight. In comparison with literature data on pneumococcal polysaccharide 6A, 19A was found to be the more labile, and hence appears to be the most labile pneumococcal polysaccharide studied to date. The rate of hydrolysis increased at higher pH and in the presence of divalent cation, but the extent was lower than expected based on similar data on RNA. Finally, the differences in the phosphodiester bond stabilities were analyzed by considering stereochemical factors in these polysaccharides. These results also provide a framework for evaluation of molecular integrity of phosphodiester-bond-containing polysaccharides in different solution conditions. Copyright 2004 Wiley Periodicals, Inc. Biopolymers, 2004
base hydrolysis, phosphodiester bond, pneumococcal polysaccharide
NCBI PubMed ID: 15307199Journal NLM ID: 0372525Publisher: Wiley Interscience
Correspondence: hari_pujar@merck.com
Institutions: Merck Research Laboratories, Merck & Co., West Point, PA 19486
- Article ID: 1346
Abeygunawardana C, Williams TC, Sumner JS, Hennessey JP "Development and validation of an NMR-based identity assay for bacterial polysaccharides" -
Analytical Biochemistry 279(2) (2000) 226-240
A method utilizing NMR spectroscopy has been developed to confirm the identity of bacterial polysaccharides used to formulate a polyvalent pneumococcal polysaccharide vaccine. The method is based on 600 MHz proton NMR spectra of individual serotype-specific polysaccharides. A portion of the anomeric region of each spectrum (5.89 to 4.64 ppm) is compared to spectra generated for designated reference samples for each polysaccharide of interest. The selected region offers a spectral window that is unique to a given polysaccharide and is sensitive to any structural alteration of the repeating units. The similarity of any two spectral profiles is evaluated using a correlation coefficient (rho), where rho >/= 0.95 between a sample and reference profile indicates a positive identification of the sample polysaccharide. This method has been shown to be extremely selective in its ability to discriminate between serotype-specific polysaccharides, some of which differ by no more than a single glycosidic linkage. Furthermore, the method is rapid and does not require extensive sample manipulations or pretreatments. The method was validated as a qualitative identity assay and will be incorporated into routine quality control testing of polysaccharide powders to be used in preparation of the polyvalent pneumococcal vaccine PNEUMOVAX 23. The specificity and reproducibility of the NMR-based identity assay is superior to the currently used colorimetric assays and can be readily adapted for use with other bacterial polysaccharide preparations as well.
NMR, Bacterial, polysaccharide, polysaccharides, Bacterial polysaccharide, bacterial polysaccharides, assay, development, identity assay, method development, validation
NCBI PubMed ID: 10706792Publication DOI: 10.1006/abio.1999.447Journal NLM ID: 0370535Publisher: Academic Press
Correspondence: abey@merck.com
Institutions: Bioprocess and Bioanalytical Research, Merck Research Laboratories, West Point, Pensylvania, USA
Methods: NMR
- Article ID: 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
- Article ID: 5473
Zou W, Li J, Vinogradov E, Cox A "Removal of cell wall polysaccharide in pneumococcal capsular polysaccharides by selective degradation via deamination" -
Carbohydrate Polymers 218 (2019) 199-207
Pneumococcal cell wall polysaccharide (C-PS), a contaminant in pneumococcal capsular polysaccharide (Pn-PS) vaccines is degraded by mild deamination of the 4-amino-2-acetamido-2,4,6-tri-deoxy-galactose (AAT) in C-PS, which was carried out by addition of 5% aqueous sodium nitrite to a solution of polysaccharide in 5% aqueous acetic acid. Glycosidic linkage and functional groups such as O-acetates, phosphodiesters, and pyruvates were preserved under the conditions. The small fragments from degraded C-PS were removed by ultrafiltration or dialysis to provide essentially C-PS free Pn-PS. Because of the presence of AAT in its structure the deamination is not suitable for the purification of type 1 Pn-PS. Meanwhile, the mass and NMR spectroscopic analysis on the deamination products suggests that both type 1 Pn-PS and C-PS degraded following a major pathway of 5,4-hydride shift, cleavage of AAT O5-C1 bond, C1 hemiacetal formation, and its hydrolysis to release neighboring GalA- in type 1 Pn-PS and GalNAc(6-O-PCho)- in C-PS
mechanism, degradation, deamination, cell wall polysaccharide, pneumococcal capsular polysaccharide
NCBI PubMed ID: 31221321Publication DOI: 10.1016/j.carbpol.2019.03.070Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: W. Zou
Institutions: Human Health Therapeutic Research Center, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, K1A 0R6, Canada
Methods: gel filtration, 13C NMR, 1H NMR, sugar analysis, MS/MS, MS, dialysis, SEC-HPLC, ultrafiltration, mild deamination
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4. Compound ID: 1750
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a-D-Glcp-(1-2)-b-D-Galp-(1-4)-+
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-3)-a-D-GlcpNAc-(1-4)-b-D-Glcp-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_140108,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_153217,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 540
Kondakova AN, Fudala R, Bednarska K, Senchenkova SN, Knirel YA, Kaca W "Structure of the neutral O-polysaccharide and biological activities of the lipopolysaccharide of Proteus mirabilis O20" -
Carbohydrate Research 339(3) (2004) 623-628
Mild acid degradation of the lipopolysaccharide (LPS) of Proteus mirabilis O20 resulted in depolymerisation of the O-polysaccharide to give a repeating-unit pentasaccharide. A polysaccharide was obtained by O-deacylation of the LPS followed by nitrous acid deamination. The derived pentasaccharide and polysaccharide were studied by NMR spectroscopy, including 2D 1H,1H COSY, TOCSY, ROESY, 1H,13C HMQC and HMQC-TOSCY experiments, along with chemical methods, and the following structure of the repeating unit of the O-polysaccharide was established: [Carbohydrate structure: see text]. As opposite to most other P. mirabilis O-polysaccharides studied, that of P. mirabilis O20 is neutral. A week serological cross-reactivity was observed between anti-P. mirabilis O20 serum and LPS of a number of Proteus serogroups with known O-polysaccharide structure. The ability of LPS of P. mirabilis O20 to activate the serine protease cascade was tested in Limulus amoebocyte lysate and in human blood plasma and compared with that of P. mirabilis O14a,14c having an acidic O-polysaccharide. The LPS of P. mirabilis O20 was found to be less active in both assays than the LPS of P. mirabilis O14a,14c and, therefore, the structurally variable O-polysaccharide may influenced the biological activity of the conserved lipid A moiety of the LPS.
Lipopolysaccharide, Proteus mirabilis, O-Polysaccharide structure, Serological cross-reactivity, Blood serum
NCBI PubMed ID: 15013399Publication DOI: 10.1016/j.carres.2003.11.016Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: rafalfu@wp.pl
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 for Medical Biology and Microbiology, Polish Academy of Sciences,93-232 Lodz, Poland, Institute of Microbiology, Swietokrzyska Academy, Kielce 25-406, Poland
Methods: NMR-2D, methylation, NMR, sugar analysis
- Article ID: 1589
Zych K, Perepelov AV, Baranowska A, Zablotni A, Knirel YA, Sidorczyk Z "Structure and serological studies of the O-polysaccharide of Proteus penneri 75. Epitopes and subgroups of Proteus serogroup O73" -
FEMS Immunology and Medical Microbiology 43(2) (2005) 141-148
The O-specific polysaccharide of the lipopolysaccharide of Proteus penneri strain 75 consists of tetrasaccharide-ribitol phosphate repeating units and resembles ribitol teichoic acids of Gram-positive bacteria. The following structure of the polysaccharide was elucidated by chemical methods and 1H and 13C NMR spectroscopy: [structure in text] where Rib-ol is ribitol. Serological studies with polyclonal antisera showed that the same structure of the O-polysaccharide occurred in two strains: P. penneri 75 and 128. A similar structure has been established earlier for the O-polysaccharide of P. penneri 103 [Drzewiecka, D., et al., Carbohydr. Res. 337 (2002) 1535-1540]. On the basis of complex serological investigations with use of two polyclonal P. penneri 75 and 103 O-antisera, five strains could be classified into Proteus O73 serogroup: P. penneri 48, 75, 90, 103 and 128, two of which (P. penneri 75 and 128) should be subdivided into subgroup 73a, 73b and three others (P. penneri 48, 90 and 103) into subgroup 73a, 73c. Epitopes responsible for the cross-reactivity of P. penneri O73 strains and a related strain of P. mirabilis O20 were tentatively defined.
structure, epitope, epitopes, O-polysaccharide, O polysaccharide, Proteus, serological, serogroup, Proteus penneri
NCBI PubMed ID: 15681143Journal NLM ID: 9315554Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of General Microbiology, Institute of Microbiology and Immunology, University of Lodz, Banacha 12/16, 90-237 Lodz, Poland
Methods: methylation, NMR, sugar analysis
- Article ID: 3868
Kabanov DS, Prokhorenko IR "Structural analysis of lipopolysaccharides from Gram-negative bacteria" -
Biochemistry (Moscow) 75(4) (2010) 383-404
This review covers data on composition and structure of lipid A, core, and O-polysaccharide of the known lipopolysaccharides from Gram-negative bacteria. The relationship between the structure and biological activity of lipid A is discussed. The data on roles of core and O-polysaccharide in biological activities of lipopolysaccharides are presented. The structural homology of some oligosaccharide sequences of lipopolysaccharides to gangliosides of human cell membranes is considered.
core, Lipooligosaccharide, O-antigen, lipid A, gangliosides, cytokines, lipopolysaccharide (endotoxin)
NCBI PubMed ID: 20618127Publication DOI: 10.1134/S0006297910040012Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: kabanovd1@rambler.ru
Institutions: Institute of Basic Biological Problems, Russian Academy of Sciences, Pushchino, Russia
- Article ID: 4042
Kaca W, Glenska J, Lechowicz L, Grabowski S, Brauner A, Kwinkowski M "Serotyping of Proteus mirabilis clinical strains based on lipopolysaccharide O-polysaccharide and core oligosaccharide structures" -
Biochemistry (Moscow) 76(7) (2011) 851-861
The aim of this work was to serotype Proteus mirabilis urinary tract infection (UTI) strains based on chemically defined O-antigens with the use of two clinical collections from Sweden and Poland consisting of 99 and 24 UTI strains, respectively. A simple two-step serotyping scheme was proposed using enzyme immunoassay with heat-stable surface antigens of Proteus cells and immunoblotting with isolated lipopolysaccharides (LPSs). Using polyclonal anti-P. mirabilis rabbit antisera, 50 Swedish and 8 Polish strains were classified into serogroups O10, O38, O36, O30, O17, O23, O9, O40, O49, O27, O5, O13, O24, O14, and O33. From the Swedish strains, 10 belonged to serogroup O10 and five to each of serogroups O38, O36, and O9. Therefore, none of the O-serogroups was predominant. The majority of the serotyped clinical strains possess acidic O-antigens containing uronic acids and various acidic non-carbohydrate substituents. In immunoblotting, antisera cross-reacted with both O-antigen and core of LPSs. The core region of 19 LPSs bound a single serum, and that of 12 LPSs bound more than two sera. Following bioinformatic analysis of the available sequences, a molecular approach to the prediction of Proteus core oligosaccharide structures was proposed. The identification of the core type of P. mirabilis R110, derived from a serogroup O3 wild strain, using restriction fragments length polymorphism analysis of galacturonic acid transferase is shown as an example. In summary, the most frequent O-serogroups among P. mirabilis UTI stains were identified. The diversity of serological reactions of LPSs is useful for serotyping of P. mirabilis clinical isolates. A possible role of the acidic components of O-antigens in UTI is discussed.
Lipopolysaccharide, O-antigen, Proteus mirabilis, serology, serotyping, glycosyl transferas
NCBI PubMed ID: 21999547Publication DOI: 10.1134/S0006297911070169Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: wieslaw.kaca@ujk.edu.pl
Institutions: Department of Microbiology, Institute of Biology, Jan Kochanowski University, Kielce, Poland
Methods: PCR, SDS-PAGE, EIA, serological methods, immunoblotting, bioinformatic analysis
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5. Compound ID: 1751
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a-D-Glcp-(1-2)-b-D-Galp-(1-4)-a-D-GlcpNAc-(1-4)-b-D-Glcp-(1-3)-b-D-GlcpNAc |
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Structure type: oligomer
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_140108,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_153217,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 540
Kondakova AN, Fudala R, Bednarska K, Senchenkova SN, Knirel YA, Kaca W "Structure of the neutral O-polysaccharide and biological activities of the lipopolysaccharide of Proteus mirabilis O20" -
Carbohydrate Research 339(3) (2004) 623-628
Mild acid degradation of the lipopolysaccharide (LPS) of Proteus mirabilis O20 resulted in depolymerisation of the O-polysaccharide to give a repeating-unit pentasaccharide. A polysaccharide was obtained by O-deacylation of the LPS followed by nitrous acid deamination. The derived pentasaccharide and polysaccharide were studied by NMR spectroscopy, including 2D 1H,1H COSY, TOCSY, ROESY, 1H,13C HMQC and HMQC-TOSCY experiments, along with chemical methods, and the following structure of the repeating unit of the O-polysaccharide was established: [Carbohydrate structure: see text]. As opposite to most other P. mirabilis O-polysaccharides studied, that of P. mirabilis O20 is neutral. A week serological cross-reactivity was observed between anti-P. mirabilis O20 serum and LPS of a number of Proteus serogroups with known O-polysaccharide structure. The ability of LPS of P. mirabilis O20 to activate the serine protease cascade was tested in Limulus amoebocyte lysate and in human blood plasma and compared with that of P. mirabilis O14a,14c having an acidic O-polysaccharide. The LPS of P. mirabilis O20 was found to be less active in both assays than the LPS of P. mirabilis O14a,14c and, therefore, the structurally variable O-polysaccharide may influenced the biological activity of the conserved lipid A moiety of the LPS.
Lipopolysaccharide, Proteus mirabilis, O-Polysaccharide structure, Serological cross-reactivity, Blood serum
NCBI PubMed ID: 15013399Publication DOI: 10.1016/j.carres.2003.11.016Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: rafalfu@wp.pl
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 for Medical Biology and Microbiology, Polish Academy of Sciences,93-232 Lodz, Poland, Institute of Microbiology, Swietokrzyska Academy, Kielce 25-406, Poland
Methods: NMR-2D, methylation, NMR, sugar analysis
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6. Compound ID: 2179
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D-Gro-(1--P--3)--+
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-4)-b-D-Glcp-(1-4)-b-D-Galp-(1-4)-a-D-Glcp-(1-3)-a-L-Rhap-(1-
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a-D-Glcp3Ac-(1-2)-+ |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130695,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153217,IEDB_158539,IEDB_190606,IEDB_225177,IEDB_885823,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: 699
Jiang SM, Wang L, Reeves PR "Molecular characterization of Streptococcus pneumoniae type 4, 6B, 8, and 18C capsular polysaccharide gene clusters" -
Infection and Immunity 69(3) (2001) 1244-1255
Capsular polysaccharide (CPS) is a major virulence factor in Streptococcus pneumoniae. CPS gene clusters of S. pneumoniae types 4, 6B, 8, and 18C were sequenced and compared with those of CPS types 1, 2, 14, 19F, 19A, 23F, and 33F. All have the same four genes at the 5' end, encoding proteins thought to be involved in regulation and export. Sequences of these genes can be divided into two classes, and evidence of recombination between them was observed. Next is the gene encoding the transferase for the first step in the synthesis of CPS. The predicted amino acid sequences of these first sugar transferases have multiple transmembrane segments, a feature lacking in other transferases. Sugar pathway genes are located at the 3' end of the gene cluster. Comparison of the four dTDP-L-rhamnose pathway genes (rml genes) of CPS types 1, 2, 6B, 18C, 19F, 19A, and 23F shows that they have the same gene order and are highly conserved. There is a gradient in the nature of the variation of rml genes, the average pairwise difference for those close to the central region being higher than that for those close to the end of the gene cluster and, again, recombination sites can be observed in these genes. This is similar to the situation we observed for rml genes of O-antigen gene clusters of Salmonella enterica. Our data indicate that the conserved first four genes at the 5' ends and the relatively conserved rml genes at the 3' ends of the CPS gene clusters were sites for recombination events involved in forming new forms of CPS. We have also identified wzx and wzy genes for all sequenced CPS gene clusters by use of motifs.
Streptococcus pneumoniae, capsular polysaccharide, gene cluster
NCBI PubMed ID: 11179285Publication DOI: 10.1128/IAI.69.3.1244-1255.2001Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: reeves@angis.usyd.edu.au
Institutions: Department of Microbiology, The University of Sydney, Sydney, New South Wales 2006, Australia
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7. Compound ID: 2213
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D-Gro-(1--P--3)--+
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-4)-b-D-Glcp-(1-4)-b-D-Galp-(1-4)-a-D-Glcp-(1-3)-b-L-Rhap-(1-
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a-D-Glcp-(1-2)-+ |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130695,IEDB_136044,IEDB_137472,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_146668,IEDB_153217,IEDB_190606,IEDB_225177,IEDB_885823,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: 718
Karlsson C, Jansson PE, Widmalm G, Sorensen UBS "Structural elucidation of the capsular polysaccharide from Streptococcus pneumoniae type 18B" -
Carbohydrate Research 304(2) (1997) 165-172
The structure of the capsular polysaccharide from Streptococcus pneumoniae type 18B has been determined using NMR spectroscopy and methylation analysis as the principal methods. It is concluded that the polysaccharide is composed of pentasaccharide repeating units with a glycerol phosphate substituting the 3-position of the branch point residue. The carbohydrate backbone in type 18B is identical to that in S. pneumoniae type 18F but without the O-acetyl groups present in that type. [formula: see text] In this structure, the absolute configuration of the glycerol phosphate moiety has not been determined but should be D, in analogy with that determined for the capsular polysaccharide from S. pneumoniae type 18A [T. Rundlöf, G. Widmalm, Anal. Biochem., 243 (1996) 228-233].
structural, capsular, polysaccharide, Streptococcus, Streptococcus pneumoniae, capsular polysaccharide, type, elucidation, NMR structure, Pneumococcus
NCBI PubMed ID: 9449767Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: pjansson@kfc.ki.se
Institutions: Clinical Research Centre, Analitycal Unit, Karolinska Institute, Huddinge Hospital, Huddinge, Sweden
Methods: NMR
- Article ID: 4827
Geno KA, Gilbert GL, Song JY, Skovsted IC, Klugman KP, Jones C, Konradsen HB, Nahm MH "Pneumococcal Capsules and Their Types: Past, Present, and Future" -
Clinical Microbiology Reviews 28(3) (2015) 871-899
Streptococcus pneumoniae (the pneumococcus) is an important human pathogen. Its virulence is largely due to its polysaccharide capsule, which shields it from the host immune system, and because of this, the capsule has been extensively studied. Studies of the capsule led to the identification of DNA as the genetic material, identification of many different capsular serotypes, and identification of the serotype-specific nature of protection by adaptive immunity. Recent studies have led to the determination of capsular polysaccharide structures for many serotypes using advanced analytical technologies, complete elucidation of genetic basis for the capsular types, and the development of highly effective pneumococcal conjugate vaccines. Conjugate vaccine use has altered the serotype distribution by either serotype replacement or switching, and this has increased the need to serotype pneumococci. Due to great advances in molecular technologies and our understanding of the pneumococcal genome, molecular approaches have become powerful tools to predict pneumococcal serotypes. In addition, more-precise and -efficient serotyping methods that directly detect polysaccharide structures are emerging. These improvements in our capabilities will greatly enhance future investigations of pneumococcal epidemiology and diseases and the biology of colonization and innate immunity to pneumococcal capsules.
serotype, Streptococcus pneumoniae, vaccines, Pneumococcal Capsules
NCBI PubMed ID: 26085553Publication DOI: 10.1128/CMR.00024-15Journal NLM ID: 8807282Publisher: Washington, DC: American Society for Microbiology
Correspondence: Moon H. Nahm
Institutions: Department of Pathology, University of Alabama at Birmingham, Birmingham, Alabama, USA, Centre for Infectious Diseases and Microbiology, Institute of Clinical Pathology & Medical Research, Westmead Hospital, Wentworthville, New South Wales, Australia, Marie Bashir Institute for Infectious Diseases and Biosecurity, University of Sydney, Sydney, New South Wales, Australia, Division of Infectious Disease, Department of Internal Medicine, Korea University Guro Hospital, Seoul, South Korea, SSI Diagnostica, Division of Microbiology and Diagnostics, Statens Serum Institut, Copenhagen, Denmark, Pneumonia Program Strategy Team, Bill & Melinda Gates Foundation, Seattle, Washington, USA, Laboratory for Molecular Structure, NIBSC, South Mimms, Herts, United Kingdom, Department of Microbiology, University of Alabama at Birmingham, Birmingham, Alabama, USA
- Article ID: 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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8. Compound ID: 2541
|
a-Abep4Ac-(1-3)-+ a-D-Glcp-(1-2)-+
| |
-4)-b-L-Rhap-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-3)-b-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_136044,IEDB_136104,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_153217,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_136,SB_165,SB_166,SB_187,SB_192,SB_195,SB_196,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 865
Kocharova NA, Knirel YA, Stanislavsky ES, Kholodkova EV, Lugowski C, Jachymek W, Romanowska E "Structural and serological studies of lipopolysaccharides of Citrobacter O35 and O38 antigenically related to Salmonella" -
FEMS Immunology and Medical Microbiology 13(1) (1996) 1-8
Structural analysis using 13C NMR spectroscopy and methylation showed that lipopolysaccharides (LPSs) of Citrobacter freundii O35 and Salmonella arizonae O59 have structurally identical O-specific polysaccharide chains, and those of C. freundii O38 and Salmonella kentucky differ only in the presence of O-acetyl groups in the former. Serological relationships between the structurally similar LPSs were demonstrated using inhibition of ELISA, rocket immunoelectrophoresis, double gel diffusion, and immunoblotting. The O-acetyl groups present in C. freundii O38 LPS are of little importance for its serological specificity. A cross-reaction was observed in immunoblotting between O-antisera to C. freundii O35 and S. arizonae O59 and a structurally related LPS of Pseudomonas aeruginosa O11a, 11b (Lanyi-Bergan classification).
Lipopolysaccharide, structure, Pseudomonas aeruginosa, O-specific polysaccharide, Salmonella, Citrobacter, immunospecificity, O-acetyl group
NCBI PubMed ID: 8821392Publication DOI: 10.1111/j.1574-695X.1996.tb00209.xJournal NLM ID: 9315554Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: 13C NMR, methylation
- Article ID: 1467
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: 3706
Katzenellenbogen E, Kocharova NA, Toukach FV, Gorska S, Korzeniowska-Kowal A, Bogulska M, Gamian A, Knirel YA "Structure of an abequose-containing O-polysaccharide from Citrobacter freundii O22 strain PCM 1555" -
Carbohydrate Research 344(13) (2009) 1724-1728
The lipopolysaccharide of Citrobacter freundii O22 (strain PCM 1555) was degraded under mild acidic conditions and the O-polysaccharide released was isolated by gel chromatography. Sugar and methylation analyses along with 1H and 13C NMR spectroscopy, including two-dimensional 1H,1H ROESY and 1H,13C HMBC experiments, showed that the repeating unit of the O-polysaccharide has the following structure: where Abe is abequose (3,6-dideoxy-d-xylo-hexose). SDS-PAGE and immunoblotting revealed that the O-antigen of C. freundii O22 is serologically indistinguishable from those of Salmonella group B serovars (Typhimurium, Brandenburg, Sandiego, Paratyphi B) but not related to other abequose-containing O-antigens tested (Citrobacter werkmanii O38 and Salmonella Kentucky) or colitose (l enantiomer of abequose)-containing O-antigen of Escherichia coli O111.
Lipopolysaccharide, endotoxin, O-Specific polysaccharide structure, serological classification, Citrobacter, Citrobacter freundii
NCBI PubMed ID: 19576576Publication DOI: 10.1016/j.carres.2009.06.005Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: katzenel@iitd.pan.wroc.pl (E. Katzenellenbogen)
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation, L.Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wrocław, Poland, Department of Medical Biochemistry, Wrocław Medical University, Wrocław, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, SDS-PAGE, sugar analysis, acid hydrolysis, serological methods
- Article ID: 4328
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
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9. Compound ID: 2542
|
a-Abep-(1-3)-+
|
a-D-Glcp-(1-2)-+ |
| |
-2)-a-D-Manp-(1-2)-a-D-Manp-(1-3)-b-D-Galp-(1-4)-b-L-Rhap-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_136044,IEDB_136104,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_153217,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_136,SB_165,SB_166,SB_187,SB_192,SB_195,SB_196,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 865
Kocharova NA, Knirel YA, Stanislavsky ES, Kholodkova EV, Lugowski C, Jachymek W, Romanowska E "Structural and serological studies of lipopolysaccharides of Citrobacter O35 and O38 antigenically related to Salmonella" -
FEMS Immunology and Medical Microbiology 13(1) (1996) 1-8
Structural analysis using 13C NMR spectroscopy and methylation showed that lipopolysaccharides (LPSs) of Citrobacter freundii O35 and Salmonella arizonae O59 have structurally identical O-specific polysaccharide chains, and those of C. freundii O38 and Salmonella kentucky differ only in the presence of O-acetyl groups in the former. Serological relationships between the structurally similar LPSs were demonstrated using inhibition of ELISA, rocket immunoelectrophoresis, double gel diffusion, and immunoblotting. The O-acetyl groups present in C. freundii O38 LPS are of little importance for its serological specificity. A cross-reaction was observed in immunoblotting between O-antisera to C. freundii O35 and S. arizonae O59 and a structurally related LPS of Pseudomonas aeruginosa O11a, 11b (Lanyi-Bergan classification).
Lipopolysaccharide, structure, Pseudomonas aeruginosa, O-specific polysaccharide, Salmonella, Citrobacter, immunospecificity, O-acetyl group
NCBI PubMed ID: 8821392Publication DOI: 10.1111/j.1574-695X.1996.tb00209.xJournal NLM ID: 9315554Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: 13C NMR, methylation
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10. Compound ID: 3014
|
a-D-Galp-(1-2)-a-L-Rhap-(1-3)-+ a-D-Glcp-(1-2)-+
| |
-4)-b-D-Manp-(1-4)-b-D-Manp-(1-4)-a-D-Galp-(1-3)-b-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_134623,IEDB_136044,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_152206,IEDB_153217,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_918314,IEDB_983930,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_44,SB_7,SB_72,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1079
Paramonov NA, Parolis LAS, Parolis H, Boán IF, Antón J, Rodríguez-Valera F "The structure of the exocellular polysaccharide produced by the Archaeon Haloferax gibbonsii (ATCC33959)" -
Carbohydrate Research 309(1) (1998) 89-94
The structure of the neutral exocellular polysaccharide isolated from the Archaeon Haloferax gibbonsii (ATCC33959) has been determined using acid hydrolysis, methylation analysis and NMR spectroscopy. The polysaccharide contained D-Man, D-Glc, D-Gal and L-Rha in the ratios 2:1:3:1. The substitution patterns of the sugar residues were deduced from the methylation analysis which indicated the polymer to be composed of a heptasaccharide repeating unit containing two branches. The 1H and 13C NMR resonances of the component sugars were assigned using COSY, HOHAHA, HMQC, and HMQC-TOCSY 2D NMR experiments and the sequence of the sugars in the repeating unit was determined from NOESY and HMBC experiments. The structure can be written as: [formula: see text]
structure, polysaccharide, exocellular, exocellular polysaccharide, NMR spectroscopy, Archaeon, Haloferax, Haloferax gibbonsii
NCBI PubMed ID: 9720239Journal NLM ID: 0043535Publisher: Elsevier
Institutions: School of Pharmaceutical Sciences, Rhodes University, Grahamstown 6140, South Africa, Departamento de Biotecnologia, Division de Microbiologia, Universidad de Alicante, Apdo. 99, E-03080 Alicante, Spain, Departamento de Microbiologia, Faculdad de Medicina, Universidad Miguel Hernandez, E-03550 San Juan, Alicante, Spain
Methods: NMR-2D, methylation, NMR, acid hydrolysis
- Article ID: 5137
Casillo A, Lanzetta R, Parrilli M, Corsaro MM "Exopolysaccharides from Marine and Marine Extremophilic Bacteria: Structures, Properties, Ecological Roles and Applications" -
Marine Drugs 16(2) (2018) pii E69
The marine environment is the largest aquatic ecosystem on Earth and it harbours microorganisms responsible for more than 50% of total biomass of prokaryotes in the world. All these microorganisms produce extracellular polymers that constitute a substantial part of the dissolved organic carbon, often in the form of exopolysaccharides (EPS). In addition, the production of these polymers is often correlated to the establishment of the biofilm growth mode, during which they are important matrix components. Their functions include adhesion and colonization of surfaces, protection of the bacterial cells and support for biochemical interactions between the bacteria and the surrounding environment. The aim of this review is to present a summary of the status of the research about the structures of exopolysaccharides from marine bacteria, including capsular, medium released and biofilm embedded polysaccharides. Moreover, ecological roles of these polymers, especially for those isolated from extreme ecological niches (deep-sea hydrothermal vents, polar regions, hypersaline ponds, etc.), are reported. Finally, relationships between the structure and the function of the exopolysaccharides are discussed.
NMR, capsular polysaccharide, exopolysaccharide, exopolysaccharides, EPS, purification, Extremophile, marine, chemical characterization, GC-MS, structure/activity relationship
NCBI PubMed ID: 29461505Publication DOI: 10.3390/md16020069Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: corsaro@unina.it; angela.casillo@unina.it
Institutions: Department of Chemical Sciences, University of Naples 'Federico II', Naples 80126, Italy
- Article ID: 5444
Hamidi M, Mirzaei R, Delattre C, Khanaki K, Pierre G, Gardarin C, Petit E, Karimitabar F, Faezi S "Characterization of a new exopolysaccharide produced by Halorubrum sp. TBZ112 and evaluation of its anti-proliferative effect on gastric cancer cells" -
3 Biotech 9(1) (2019) 1
In the present study, we aimed to extract, purify, analyze monosaccharide composition of exopolysaccharide (EPS) produced by Halorubrum sp. TBZ112 (KCTC 4203 and IBRC-M 10773) and also to evaluate its possible antiproliferative activity against human gastric cancer (MKN-45) cell line and its biocompatibility effect on normal cells using human dermal fibroblast (HDF) cell line. Average molecular weight and monosaccharide composition were determined by high-pressure size exclusion chromatography (HPSEC) with multi-angle laser light scattering (MALLS) and high-pressure anion exchange chromatography (HPAEC), respectively. Fourier transform infrared (FTIR) spectroscopy was used for the partial characterization of the EPS. The EPS effect on the cell proliferation and viability of MKN-45 and HDF cells was assessed using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and trypan blue dye exclusion, respectively. Strain TBZ112 excreted 480 mg.l-1 of the EPS under optimal growth conditions. The EPS had a molecular weight of 5.052 kDa and was a heteropolysaccharide containing ten moieties mainly composed of mannose (19.95%), glucosamine (15.55%), galacturonic acid (15.43%), arabinose (12.24%), and glucuronic acid (12.05%). No significant difference of the EPS treatments on the proliferation activity of MKN-45 and HDF cells were observed (P > 0.05). For the first time, the EPS from Halorubrum sp. TBZ112, an extremely halophilic archaeon related to Halorubrum genus, was isolated and chemically characterized. The EPS from Halorubrum sp. TBZ112 possesses a relatively low molecular weight and might be applied as a biocompatible compound. More investigations are needed to determine other biological activities of the EPS along with further details of its chemical structure.
exopolysaccharide (EPS), Antiproliferative effect, Halorubrum sp.TBZ112, Monosaccharide composition
NCBI PubMed ID: 30555767Publication DOI: 10.1007/s13205-018-1515-5Journal NLM ID: 101565857Publisher: Berlin: Springer
Correspondence: Korosh Khanaki
;
Institutions: Medical Biotechnology Research Center, School of Paramedicine, Guilan University of Medical Sciences, Rasht, Iran, Institut Pascal UMR CNRS 6602, Université Clermont Auvergne, F-63000 Clermont-Ferrand, France, EA3900 BIOPI, Université de Picardie Jules Verne, Avenue des facultés, Le Bailly, 80025 Amiens cedex, France
Methods: HPAEC, FTIR, composition analysis, HPSEC-MALLS, extraction, statistical analysis
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11. Compound ID: 3116
|
R-3HOBut-(1-3)-+ a-D-Glc-(1-2)-+
| |
-2)-b-D-Glcp-(1-2)-b-D-Fucp3N-(1-6)-a-D-GlcpNAc-(1-4)-b-D-Galp-(1-3)-b-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer biological repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_147450,IEDB_151531,IEDB_153217,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_23,SB_24,SB_7,SB_8,SB_88
The structure is contained in the following publication(s):
- Article ID: 1134
Ravenscroft N, Dabrowski J, Romanowska E "Structural elucidation of the biological repeating unit of O-specific polysaccharide from Citrobacter serotype O41" -
European Journal of Biochemistry 229 (1995) 299-307
Sugar analysis of the O-specific polysaccharide produced by Citrobacter serotype O41 revealed the presence of a hexasaccharide repeating unit, which includes the unusual 3-amino-N-(D-3'-hydroxybutyryl)-3,6-dideoxy-D-galactosyl residue (Fuc3NAcyl). The structure of the repeating unit was determined by extensive use of homo- and heteronuclear two-dimensional NMR spectroscopy, including the application of long-range 1H-13C correlation experiments and NOE studies to establish the sequence of sugar units. Indentification of the Glc β1→2 Fuc3NAcyl β1→6 GlcNAc α1→ sequence at the non-reducing terminus establishes the biological repeating unit of this O-specific polysaccharide as: →2 Glc β1→ Fuc3NAcyl β1→6 GlcNAc α1→ (Glc α1→2) 4Gal β1→3 GalNAc β1→. This structure is similar to that found for the O-specific polysaccharide isolated from Hafnia alvei strain 1211 [Katzenellenbogen, E., Romanowska, E., Dabrowski, U. & Dabrowski, J. (1991) Eur. J. Biochem. 200, 401-407], which differs in having an acetyl substituent at O4 of the Fuc3NAcyl residue and a branch point of GalNAc α substituted by Glc β at O3; these differences are responsible for the only weak serological cross-reactivity of the two strains.
Lipopolysaccharide, 6-dideoxy-D-galactose, endotoxin, Citrobacter, 3-amino-N-(D-3'-hydroxybutyryl)-3
NCBI PubMed ID: 7744044Publication DOI: 10.1111/j.1432-1033.1995.0299l.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Max-Planck-Institut fur Medizinische Forschung, Heidelberg, Germany
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, periodate oxidation
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12. Compound ID: 3761
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Gro-(1--P--3)--+
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-4)-b-D-Glcp-(1-4)-b-D-Galp-(1-4)-a-D-Glcp-(1-3)-a-L-Rhap-(1-
|
a-Glcp-(1-2)-+ |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130695,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153217,IEDB_158539,IEDB_190606,IEDB_225177,IEDB_885823,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: 1306
Zamze S, Martinez-Pomares L, Jones H, Taylor PR, Stillion RJ, Gordon S, Wong SY "Recognition of bacterial capsular polysaccharides and lipopolysaccharides by the macrophage mannose receptor" -
Journal of Biological Chemistry 277(44) (2002) 41613-41623
The in vitro binding of the macrophage mannose receptor to a range of different bacterial polysaccharides was investigated. The receptor was shown to bind to purified capsular polysaccharides from Streptococcus pneumoniae and to the lipopolysaccharides, but not capsular polysaccharides, from Klebsiella pneumoniae. Binding was Ca(2+)- dependent and inhibitable with d-mannose. A fusion protein of the mannose receptor containing carbohydrate recognition domains 4-7 and a full-length soluble form of the mannose receptor containing all domains external to the transmembrane region both displayed very similar binding specificities toward bacterial polysaccharides, suggesting that domains 4-7 are sufficient for recognition of these structures. Surprisingly, no direct correlation could be made between polysaccharide structure and binding to the mannose receptor, suggesting that polysaccharide conformation may play an important role in recognition. The full-length soluble form of the mannose receptor was able to bind simultaneously both polysaccharide via the carbohydrate recognition domains and sulfated oligosaccharide via the cysteine-rich domain. The possible involvement of the mannose receptor, either cell surface or soluble, in the innate and adaptive immune responses to bacterial polysaccharides is discussed
Lipopolysaccharide, conformation, lipopolysaccharides, oligosaccharide, structure, correlation, Bacterial, role, capsular, polysaccharide, Streptococcus, Streptococcus pneumoniae, D-mannose, capsular polysaccharide, capsular polysaccharides, polysaccharides, carbohydrate, cell, Research, form, recognition, involvement, protein, response, specificity, Klebsiella, Bacterial polysaccharide, region, external, surface, polysaccharide structure, purified, Klebsiella pneumoniae, bacterial polysaccharides, binding, domain, domains, vaccine, immune response, Mannose, immune, in vitro, macrophage, soluble, receptor, sulfated, pathology, carbohydrate recognition, carbohydrate recognition domain, fusion, fusion protein, transmembrane
NCBI PubMed ID: 12196537Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: susanne.zamze@jenner.ac.uk
Institutions: Edward Jenner Institute for Vaccine Research, Compton, Berkshire RG20 7NN, United Kingdom and the Sir William Dunn School of Pathology, University of Oxford, South Parks Road, Oxford OX1 3RE, United Kingdom
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13. Compound ID: 3962
|
R-3HOBut-(1-3)-+ a-D-Glcp-(1-2)-+
| |
-2)-b-D-Glcp-(1-2)-b-D-Fucp3N-(1-6)-a-D-GlcpNAc-(1-4)-b-D-Galp-(1-3)-b-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_147450,IEDB_151531,IEDB_153217,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_23,SB_24,SB_7,SB_8,SB_88
The structure is contained in the following publication(s):
- Article ID: 1467
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: 4328
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: 4798
Shashkov AS, Wang M, Turdymuratov EM, Hu S, Arbatsky NP, Guo X, Wang L, Knirel YA "Structural and genetic relationships of closely related O-antigens of Cronobacter spp. and Escherichia coli: C. sakazakii G2594 (serotype O4)/E. coli O103 and C. malonaticus G3864 (serotype O1)/E. coli O29" -
Carbohydrate Research 404 (2015) 124-131
O-Antigen (O-polysaccharide) variation is the basis for bacterial serotyping and is important in bacterial virulence and niche adaptation. In this work, we present structural and genetic evidences for close relationships between the O-antigens of the Cronobacter spp. and Escherichia coli. Cronobacter sakazakii G2594 (serotype O4) and Cronobacter malonaticus G3864 (serotype O1) are structurally related to those of E. coli O103 and O29, respectively, and some other members of the Enterobacteriaceae family differing in the patterns of lateral glucosylation (C. sakazakii G2594) or O-acetylation (C. malonaticus G3864). The O-antigen gene clusters of the corresponding Cronobacter and E. coli strains contain the same genes with high-level similarity, and the structural differences within both O-antigen pairs were suggested to be due to modification genes carried by prophages.
Lipopolysaccharide, O-specific polysaccharide, bacterial polysaccharide structure, O-antigen gene cluster, Cronobacter sakazakii, Cronobacter malonaticus
NCBI PubMed ID: 25555751Publication DOI: 10.1016/j.carres.2014.11.014Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Y.A. Knirel
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, Key Laboratory of Molecular Microbiology and Technology of the Ministry of Education, College of Life Sciences, Nankai University, Tianjin, China, Tianjin Biochip Corporation, TEDA, Tianjin, China
Methods: 13C NMR, 1H NMR, NMR-2D, PCR, DNA sequencing, sugar analysis, acid hydrolysis, GLC, mild acid hydrolysis, Smith degradation, NMR-1D, GPC, UV, bioinformatic analysis
- 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
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14. Compound ID: 4106
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D-Gro-(1--P--3)--+
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-4)-b-D-Glcp-(1-4)-b-D-Galp-(1-4)-a-D-Glcp-(1-3)-b-L-Rhap-(1-
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a-D-Glcp6Ac-(1-2)-+ |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130695,IEDB_136044,IEDB_137472,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_146668,IEDB_153217,IEDB_190606,IEDB_225177,IEDB_885823,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: 1519
Jones C "NMR assays for carbohydrate-based vaccines" -
Journal of Pharmaceutical and Biomedical Analysis 38(5) (2005) 840-850
Antibodies against the cell surface carbohydrates of many microbial pathogens protect against infection. This was initially exploited by the development of purified polysaccharide vaccines, but glycoconjugate vaccines, in which the cell surface carbohydrate of a microbial pathogen is covalently attached to an appropriate carrier protein, are proving the most effective means to generate this protective immunity. Carbohydrate-based vaccines against Haemophilus influenzae Type b, Neisseria meningitidis, Streptococcus pneumoniae and Salmonella enterica serotype Typhi (S. Typhi) are already licensed, and many similar products are in various stages of development. For many of these vaccines, biological assays are not available or are inappropriate and NMR spectroscopy is proving a valuable tool for the characterisation and quality control of existing and novel products. This review highlights some of the areas in which NMR spectroscopy is currently used, and where further developments may be expected.
capsular polysaccharide, O-acetylation, pneumonia, glycoconjugate, meningitis, carbohydrate-based vaccines, identity, typhoid
NCBI PubMed ID: 16087046Publication DOI: 10.1016/j.jpba.2005.01.044Journal NLM ID: 8309336Publisher: London: Elsevier
Institutions: Laboratory for Molecular Structure, National Institute for Biological Standards and Control, South Mimms, UK
Methods: NMR
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15. Compound ID: 4542
Structure type: oligomer
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_153217,IEDB_190606,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: 1739
Simmons DAR "Immunochemistry of Shigella flexneri O-antigens: an analysis of the antigenic determinants of the basal (rough) region" -
Biochemical Society Transactions 13 (1985) 370-371
no abstract available
Publication DOI: 10.1042/bst0130370Journal NLM ID: 7506897Institutions: Department of Bacteriology and Immunology, University of Glasgow, Glasgow GI1 6NT. U.K.
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Next 15 structure(s)
Total list of structure IDs on all result pages of the current query:
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