Found 139 structures.
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1. Compound ID: 266
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a-Abep-(1-3)-+
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-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1- |
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Structure type: suggested polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_127517,IEDB_130701,IEDB_135509,IEDB_135513,IEDB_135514,IEDB_135611,IEDB_136093,IEDB_136105,IEDB_136775,IEDB_136906,IEDB_137472,IEDB_137486,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 69
Falt IC, Mills D, Schweda EKH, Timmis KN, Lindberg AA "Construction of recombinant aroA salmonellae stably producing the Shigella dysenteriae serotype 1 O-antigen and structural characterization of the Salmonella/Shigella hybrid LPS" -
Microbial Pathogenesis 20(1) (1996) 11-30
The TN501 mercury resistant transposon containing the rfp and rfb loci encoding biosynthesis of the O-antigen of Shigella dysenteriae serotype 1 lipopolysaccharide (LPS) was constructed and introduced into aroA mutants of Salmonella typhimurium and Salmonella dublin. In five recombinant strains, both homologous LPS and hybrid LPS, consisting of Salmonella lipid A-core and Shigella O-antigen, were produced. All derivatives but one (SL3235) stably inherited the new trait. Immunofluorescence microscopy, using mixtures of differentially-labelled antibodies specific for either the Salmonella or the Shigella O-antigen, demonstrated that individual bacteria produced both types of LPS. Qualitative and quantitative analysis of polysaccharides obtained by mild hydrolysis of purified LPS was carried out by methylation analysis and NMR spectroscopy, and revealed that the ratio of Salmonella to Shigella O-antigen repeating units in the high molecular weight fraction of isolated polysaccharides varied from 1.3: 1 to 8.4:1 as based on the relative proportions of 1,4,5-tri-O-acetyl-2,3-di-O-methyl-L-rhamnitol (Salmonella repeating unit) and 1,3,5-tri-O-acetyl-2,4-di-O-methyl-L-rhamnitol (Shigella repeating unit). The attachment site of the Shigella O-antigen to the Salmonella core was investigated by construction of a mutant rfp-rfb gene cluster encoding the synthesis of only one repeat unit of the Shigella dysenteriae type 1 O-antigen, and its introduction into a rough Salmonella strain. This hybrid organism produced a polysaccharide with the following structure, [formula: see text] demonstrating that the Shigella dysenteriae type 1 O-antigen is linked at position O-4 of the subterminal D-glucose unit in the Salmonella core
LPS, Salmonella, Shigella dysenteriae type 1, hybrids, vaccine.
NCBI PubMed ID: 8692007Journal NLM ID: 8606191Publisher: Academic Press
Institutions: Department of Immunology, Microbiology, Pathology and Infectious Diseases, Karolinska Institute, Huddinge Hospital, Sweden, Department of Medical Biochemistry, University of Geneva, Switzerland, Division of Microbiology, National Research Centre for Biotechnology, Braunschweig, Germany, Clinical Research Centre, Karolinska Institute, Novum, Huddinge Hospital, Sweden
- Article ID: 414
Wang L, Andrianopoulos K, Liu D, Popoff MY, Reeves PR "Extensive variation in the O-antigen gene cluster within one Salmonella enterica serogroup reveals an unexpected complex history" -
Journal of Bacteriology 184(6) (2002) 1669-1677
The 46 serogroups of Salmonella enterica have different O-antigens, and each is thought to have a specific form of the O-antigen cluster. Comparison of the 145 serovars of serogroup B revealed much more intraserogroup genetic diversity than expected. The O27 factor, due to an α 1-6 linkage between O units in place of the more common α 1-2 linkage and previously thought to be due to a converting bacteriophage, is now shown to be due to a wzy(α(1-6)) gene located within the major gene cluster. Surprisingly a remnant of this gene in all O27(-) serovars shows that the ancestor was O27(+). There are six distinct gene cluster forms, five apparently derived by a series of deletions and one by an insertion from an ancestral O27(+) form present in 57 serovars. The history of the gene cluster and movement between subspecies I and II can be traced. Two of the derivative forms still have a functional wzy(α(1-6)) gene, while in three it has been inactivated by deletion or insertion. Two of the forms lacking a functional wzy(α(1-6)) gene have the wzy(α(1-2)) gene first described for strain LT2 as rfc, whereas for the third the wzy gene has not been located
variation, O-antigen, gene cluster, specific, Salmonella, insertion, Salmonella enterica, bacteriophage, serogroup B, genetic diversity, rfc
NCBI PubMed ID: 11872718Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: reeves@angis.org.au
Institutions: Department of Microbiology, The University of Sydney, Sydney, New South Wales 2006, Australia
Methods: DNA sequencing, SDS-PAGE
- Article ID: 1369
Baxa U, Steinbacher S, Miller S, Weintraub A, Huber R, Seckler R "Interactions of phage P22 tails with their cellular receptor, Salmonella O-antigen polysaccharide" -
Biophysical Journal 71 (1996) 2040-2048
Bacteriophage P22 binds to its cell surface receptor, the repetitive O-antigen structure in Salmonella lipopolysaccharide, by its six homotrimeric tailspikes. Receptor binding by soluble tailspikes and the receptor-inactivating endorhamnosidase activity of the tailspike protein were studied using octa- and dodecasaccharides comprising two and three O-antigen repeats of Salmonella enteritidis and Salmonella typhimurium lipopolysaccharides. Wild-type tailspike protein and three mutants (D392N, D395N, and E359Q) with defective endorhamnosidase activity were used. Oligosaccharide binding to all three subunits, measured by a tryptophan fluorescence quench or by fluorescence depolarization of a coumarin label attached to the reducing end of the dodecasaccharide, occurs independently. At 10 degrees C, the binding affinities of all four proteins to oligosaccharides from both bacterial strains are identical within experimental error, and the binding constants for octa- and dodecasaccharides are 1 x 10(6) M(-1) and 2 x 10(6) M(-1), proving that two O-antigen repeats are sufficient for lipopolysaccharide recognition by the tailspike. Equilibration with the oligosaccharides occurs rapidly, but the endorhamnosidase produces only one cleavage every 100 s at 10 degrees C or about 2 min(-1) at the bacterial growth temperature. Thus, movement of virions in the lipopolysaccharide layer before DNA injection may involve the release and rebinding of individual tailspikes rather than hydrolysis of the O-antigen.
polysaccharide, O-antigen, O antigen, Salmonella, interaction, cellular, receptor, phage
NCBI PubMed ID: 8889178Journal NLM ID: 0370626Publisher: Cambridge, MA: Cell Press
Correspondence: robert.seckler@biologie.uniregensburg.de
Institutions: Universitat Regensberg, Phusikalishe Biochemie, Regensberg, Germany
- Article ID: 1408
Curd H, Liu D, Reeves PR "Relationships among the O-antigen gene clusters of Salmonella enterica groups B, D1, D2, and D3" -
Journal of Bacteriology 180(4) (1998) 1002-1007
The O antigen is an important cell wall antigen of gram-negative bacteria, and the genes responsible for its biosynthesis are located in a gene cluster. We have cloned and sequenced the DNA segment unique to the O-antigen gene cluster of Salmonella enterica group D3. This segment includes a novel O-antigen polymerase gene (wzyD3). The polymerase gives α(1→6) linkages but has no detectable sequence similarity to that of group D2, which confers the same linkage. We find the remnant of a D3-like wzy gene in the O-antigen gene clusters of groups D1 and B and suggest that this is the original wzy gene of these O-antigen gene clusters.
gene, O-antigen, O antigen, group, cluster, gene cluster, Salmonella, Salmonella enterica, relationship
NCBI PubMed ID: 9473060Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: reeves@angis.usyd.edu.au
Institutions: Department of Microbiology, The University of Sydney,Australia
- Article ID: 1743
Cygler M, Wu S, Zdanov A, Bundle DR, Rose DR "Recognition of a carbohydrate antigenic determinant of Salmonella by an antibody" -
Biochemical Society Transactions 21 (1993) 437-441
no abstract available
NCBI PubMed ID: 7689495Journal NLM ID: 7506897Institutions: Biotechnology Research Institute, NRCC, Montréal, Québec, Canada
Methods: conformation analysis
- Article ID: 1771
Brummell DA, Sharma VP, Anand NN, Bilous D, Dubuc G, Michniewicz J, MacKenzie CR, Sadowska J, Sigurskjold BW, Sinnott B, Yound NM, Bundle DR, Narang SA "Probing the combining site of an anti-carbohydrate antibody by saturation-mutagenesis: role of the heavy-chain CDR3 residues" -
Biochemistry 32 (1993) 1180-1187
Journal NLM ID: 0370623Publisher: American Chemical Society
- Article ID: 2270
Baumann H, Altman E, Bundle DR "Controlled acid hydrolysis of an O-antigen fragment yields univalent heptasaccharide haptens containing one 3,6-dideoxyhexose epitope" -
Carbohydrate Research 247 (1993) 347-354
No abstract available
O-antigen, O antigen, acid, epitope, hydrolysis, 3, fragment, hapten, 6-dideoxyhexose, PDF, Haptens, heptasaccharide
NCBI PubMed ID: 7693349Publication DOI: 10.1016/0008-6215(93)84270-gJournal NLM ID: 0043535Publisher: Elsevier
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario K1A 0R6 Canada
Methods: 13C NMR, 1H NMR, NMR-2D, partial acid hydrolysis, HPLC, phage degradation
- Article ID: 2466
Opdenakker G, Rudd PM, Ponting CP, Dwek RA "Concepts and principles of glycobiology" -
FASEB Journal 7 (1993) 1330-1337
Journal NLM ID: 8804484Publisher: Bethesda, MD: Federation of American Societies for Experimental Biology
- Article ID: 2726
Rose DR, Cygler M, To RJ, Przybylska M, Sinnott B, Bundle DR "Preliminary crystal structure analysis of an Fab specific for a Salmonella O-polysaccharide antigen" -
Journal of Molecular Biology 215 (1990) 489-492
Journal NLM ID: 2985088RPublisher: Elsevier
- Article ID: 3153
Szafranek J, Kumirska J, Czerwicka M, Kunikowska D, Dziadziuszko H, Glosnicka R "Structure and heterogeneity of the O-antigen chain of Salmonella agona lipopolysaccharide" -
FEMS Immunology and Medical Microbiology 48(2) (2006) 223-236
Lipopolysaccharide of Salmonella Agona smooth-type cells was obtained from bacteria by a hot phenol-water extraction procedure. Mild acid hydrolysis of lipopolysaccharide, followed by gel filtration, yielded the pure O-polysaccharide. Abequose, rhamnose, mannose, galactose and glucose in the molar ratio 0.8 : 1.0 : 1.0 : 1.1 : 0.5 were detected, and their linkages were established. Sugar configurations were determined by gas chromatography. Two repeating units, namely →2)-[α-Abep-(1→3)-]-α-D-Manp-(1→4)-α-L-Rhap-(1→3)-α-D-Galp-(1→ and →2)-[α-Abep-(1→3)-]-α-D-Manp-(1→4)-α-L-Rhap-(1→3)-[α-D-Glcp-(1→4)-]-α-D-Galp-(1→, were deduced from nuclear magnetic resonance studies. The effort to separate them was unsuccessful. An immunochemical test performed by means of Western blotting with anti O12 serum demonstrated that glucose was present in the longer lipopolysaccharide chains, at some distance from the core region.
Lipopolysaccharide, structure, O-antigen, O antigen, chain, Salmonella, heterogeneity, D
NCBI PubMed ID: 17064278Journal NLM ID: 9315554Publisher: Elsevier
Correspondence: janat@chem.univ.gda.pl
Institutions: Department of Chemistry, University of Gdansk, Gdansk, Poland
Methods: GC, composition analysis
- Article ID: 3285
Nnalue NA, Weintraub A, Oscarson S, Lindberg AA "Cross-reactivity between the mannan of Candida species, Klebsiella K24 polysaccharide and Salmonella C1 and E O-antigens is mediated by a terminal non-reducing b-mannosyl residue" -
European Journal of Biochemistry 220(3) (1994) 973-979
Rat monoclonal antibody MASC1-MR9 (MR9) binds to a mannan of Candida species and the O-antigenic polysaccharides of Salmonella bacteria of serogroups C1 (CO) and E (EO). Mannan and glycoconjugates comprising BSA and O-antigen polysaccharides, decasaccharide-BSA (CO-BSA) or trisaccharide-BSA (EO-BSA), inhibited each other's reactivity with MR9. The saccharides β-D-Manp-(1→6)-α-D-Manp-1-OMe, β-D-Manp(1→3)-α-D-Manp-1-OMe, β-D-Manp(1→2)-α-D-Manp-1-OMe (corresponds to the terminal non-reducing end of Salmonella serogroup C1 O-antigen) and β-D-Manp(1→4)-α-L-Rhap(1→3)-α-D-Galp-1-O-p-trifluoroacetamido aniline (corresponds to the backbone of Salmonella serogroup E O-antigen) inhibited the binding of MR9 to these antigens whereas α-D-Manp(1→3)-α-D-Manp-1-OMe and α-D-Manp(1→4)-α-L-Rhap-1-O-p-nitrophenyl did not. Saccharides (3-10 residues) of mammalian origin with terminal and internal Manp α-1→2, Manp α-1→3 and Manp α-1→6 residues also failed to inhibit at any concentration. None of the saccharides with internal β-mannosyl residue was able to inhibit the MR9 antibody. Monosaccharides D-mannose, β-D-Manp-1-OMe and 1,5 anhydro-D-mannitol inhibited the MR9 monoclonal antibody whereas α-D-Manp-1-OMe, β-D-Glcp-1-OMe, and β-D-Galp-1-OMe did not. In addition a Klebsiella K24 capsular polysaccharide containing a β-D-Manp(1→4)-α-D-GlcA (GlcA, glucuronic acid) as a structural element possessed an inhibitory activity. MR9 therefore recognizes an epitope within β-mannose monosaccharide residues at the terminal non-reducing ends of carbohydrate chains in mannan, and polysaccharides in Salmonella serogroups CO and EO and Klebsiella K24.
O-antigen, epitope, monoclonal antibodies, capsular polysaccharide, serogroup, Salmonella, Klebsiella, cross-reactivity, Candida
NCBI PubMed ID: 7511532Publication DOI: 10.1111/j.1432-1033.1994.tb18701.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Immunology, Microbiology, Pathology and Infectious Diseases, Karolinska Institute, Huddinge University Hospital, Sweden.
Methods: serological methods
- Article ID: 3442
Bogomolnaya LM, Santiviago CA, Yang HJ, Baumler AJ, Andrews-Polymenis HL "'Form Variation' of the O12 Antigen is Critical for Persistence of Salmonella typhimurium in the Murine Intestine" -
Molecular Microbiology 70(5) (2008) 1105-1119
S. enterica subspecies I (ssp.I) serotypes are responsible for the vast majority of salmonellosis in mammals and birds, yet only a few factors specific to this group that allow them to persist in this niche have been identified. We show that STM0557, a ssp. I specific gene encoding an inner membrane protein, is critical for fecal shedding and intestinal persistence of Salmonella enterica serotype Typhimurium ATCC14028 in Salmonella-resistant mice, but mutations in this gene do not diminish short-term intestinal colonization or invasion of cultured epithelial cells. STM0557 and two neighboring genes, located on a pathogenicity island termed SPI-16, resemble genes of the gtrA,B, gtr(type) cluster in seroconverting bacteriophages. In general, the gtr genes encode proteins responsible for serotype conversion of the infected bacterium by addition glucose residues to repeating O-antigen subunits of lipopolysaccharide (LPS). In lysogenized Shigella, such modifications have been previously shown to be constitutively expressed and to facilitate invasion of host cells. We show that serotype Typhimurium gtr orthologs, STM0557-0559, are responsible for 'form variation' or glucosylation of the O12 antigen galactose (4 position) to generate the 12-2 variant. Form variation in Typhimurium is not constitutive, but occurred upon exposure and during intracellular growth of serotype Typhimurium in J774 macrophages. Our data suggest that the 12-2 antigen is a S. enterica subspecies I specific LPS modification that enhances long-term intestinal colonization, and is in contrast to the role of O-antigen variation described for Shigella.
O-antigen, cluster, Salmonella enterica, Salmonella typhimurium, serotype conversion, murine, colonization, salmonellosis, epithelial cell
NCBI PubMed ID: 18826410Publication DOI: 10.1111/j.1365-2958.2008.06461.xJournal NLM ID: 8712028Publisher: Blackwell Publishing
Correspondence: handrews@medicine.tamhsc.edu
Institutions: Department of Microbial and Molecular Pathogenesis, College of Medicine, Texas A&M University System Health Science Center, 407 Joe H. Reynolds Medical Building, College Station, TX 77843-1114, USA
Methods: GC, MALDI-TOF MS, composition analysis, serological methods, genetic methods
- Article ID: 3578
Kaczyński Z, Gajdus J, Dziadziuszko H, Stepnowski P "Chemical structure of the somatic antigen isolated from Salmonella Abortusequi (O4)" -
Journal of Pharmaceutical and Biomedical Analysis 50(4) (2009) 679-682
A neutral O-specific polysaccharide was obtained by mild acid hydrolysis of the lipopolysaccharide (LPS) of Salmonella Abortusequi O4 bacterium (previously serogroup B). As determined by compositional analyses and NMR spectroscopy, the O-polysaccharide consists of four or five residues in the repeating subunit. The assigned structures are: and A distribution of the repeating units in O-chain was analysed by Western blotting with anti O12 serum and MS spectrometry of oligosaccharides obtained from partial hydrolysis of polysaccharide
NMR, structure, O-polysaccharide, Salmonella abortusequi
NCBI PubMed ID: 19058946Publication DOI: 10.1016/j.jpba.2008.10.013Journal NLM ID: 8309336Publisher: London: Elsevier
Correspondence: Z. Kaczyński
Institutions: Faculty of Chemistry, University of Gdansk, Gdansk, Poland
Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, FAB-MS, partial acid hydrolysis, SDS-PAGE, sugar analysis, GLC, Western blotting, composition analysis, NMR-1D, immunoblotting
- Article ID: 3707
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, methylation, GLC-MS, NMR-2D, SDS-PAGE, sugar analysis, acid hydrolysis, serological methods
- Article ID: 4315
Hong Y, Cunneen MM, Reeves PR "The Wzx translocases for Salmonella enterica O-antigen processing have unexpected serotype specificity" -
Molecular Microbiology 84(4) (2012) 620-630
Most Gram-negative bacteria have an O antigen, a polysaccharide with many repeats of a short oligosaccharide that is a part of the lipopolysaccharide, the major lipid in the outer leaflet of the outer membrane. Lipopolysaccharide is variable with 46 forms in Salmonella enterica that underpin the serotyping scheme. Repeat units are assembled on a lipid carrier that is embedded in the cell membrane, and are then translocated by the Wzx translocase from the cytoplasmic face to the outer face of the cell membrane, followed by polymerization. The O antigen is then incorporated into lipopolysaccharide and exported to the outer membrane. The Wzx translocase is widely thought to be specific only for the first sugar of the repeat unit, despite extensive variation in both O antigens and Wzx translocases. However, we found for S. enterica groups B, D2 and E that Wzx translocation exhibits significant specificity for the repeat-unit structure, as variants with single sugar differences are translocated with lower efficiency and little long-chain O antigen is produced. It appears that Wzx translocases are specific for their O antigen for normal levels of translocation.
O-antigen, Salmonella enterica, wzx
NCBI PubMed ID: 22497246Publication DOI: 10.1111/j.1365-2958.2012.08048.xJournal NLM ID: 8712028Publisher: Blackwell Publishing
Correspondence: peter.reeves@sydney.edu.au
Institutions: School of Molecular Bioscience, The University of Sydney, Sydney, NSW, Australia
Methods: SDS-PAGE, genetic methods
- Article ID: 4327
Katzenellenbogen E, Kocharova NA, Toukach PV, Gorska S, Bogulska M, Gamian A, Knirel YA "Structures of a unique O-polysaccharide of Edwardsiella tarda PCM 1153 containing an amide of galacturonic acid with 2-aminopropane-1,3-diol and an abequose-containing O-polysaccharide shared by E. tarda PCM 1145, PCM 1151 and PCM 1158" -
Carbohydrate Research 355 (2012) 56-62
Lipopolysaccharides of four strains of Edwardsiella tarda were degraded by mild acid hydrolysis, and the released O-polysaccharides were isolated by GPC and studied by sugar and methylation analyses along with (1)H and (13)C NMR spectroscopy, including 2D (1)H, (1)H COSY, TOCSY, ROESY, (1)H, (13)C HMBC, HSQC and HSQC-TOCSY experiments. The O-polysaccharide from E. tarda PCM 1153 was found to contain D-GalA, D-GlcNAc, D-Gal and 2-amino-1,3-propanediol (GroN). In the tetrasaccharide repeating unit, GroN is amide-linked to one of the GalA residues, and Gal is non-stoichiometrically 2- or 3-O-acetylated (~45% at each position): [structure: see text]. Three other E. tarda strains examined (PCM 1145, PCM 1151 and PCM 1158) share the following O-polysaccharide structure: [structure: see text] where Abe indicates 3,6-dideoxy-D-xylo-hexose (abequose). This structure resembles those of Citrobacter freundii O22 (PCM 1555) and Salmonella enterica O4. In accordance with the structural data, SDS-PAGE and immunoblotting of the lipopolysaccharides with anti-C. freundii O22 serum demonstrated that the O-antigens of the three E. tarda strains are serologically identical to each other and to the O-antigens of C. freundii O22 and S. enterica O4.
Lipopolysaccharide, O-antigen, bacterial polysaccharide structure, 2-Amino-2-deoxyglycerol, abequose, Edwardsiella tarda
NCBI PubMed ID: 22578768Publication DOI: 10.1016/j.carres.2012.04.004Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: katzenel@iitd.pan.wroc.pl
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Medical Biochemistry, Wrocław Medical University, Wrocław, Poland, L. Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wrocław, Poland
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, SDS-PAGE, sugar analysis, de-O-acetylation, NMR-1D, GPC, immunoblotting
- 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: 4381
Rynkiewicz MJ, Lu Z, Hui JH, Sharon J, Seaton BA "Structural Analysis of a Protective Epitope of the Francisella tularensis O-Polysaccharide" -
Biochemistry 51(28) (2012) 5684-2694
Francisella tularensis (Ft), the Gram-negative facultative intracellular bacterium that causes tularemia, is considered a biothreat because of its high infectivity and the high mortality rate of respiratory disease. The Ft lipopolysaccharide (Ft LPS) is thought to be a main protective antigen in mice and humans, and we have previously demonstrated the protective effect of the Ft LPS-specific monoclonal antibody Ab52 in a mouse model of respiratory tularemia. Immunochemical characterization has shown that the epitope recognized by Ab52 is contained within two internal repeat units of the O-polysaccharide [O-antigen (OAg)] of Ft LPS. To further localize the Ab52 epitope and understand the molecular interactions between the antibody and the saccharide, we determined the X-ray crystal structure of the Fab fragment of Ab52 and derived an antibody-antigen complex using molecular docking. The docked complex, refined through energy minimization, reveals an antigen binding site in the shape of a large canyon with a central pocket that accommodates a V-shaped epitope consisting of six sugar residues, α-D-GalpNAcAN(1→4)-α-D-GalpNAcAN(1→3)-β-D-QuipNAc(1→2)-β-D-Quip4NFm(1→4)-α-D-GalpNAcAN(1→4)-α-D-GalpNAcAN. These results inform the development of vaccines and immunotherapeutic/immunoprophylactic antibodies against Ft by suggesting a desired topology for binding of the antibody to internal epitopes of Ft LPS. This is the first report of an X-ray crystal structure of a monoclonal antibody that targets a protective Ft B cell epitope.
Lipopolysaccharide, antigen, O-antigen, X-ray, epitope, monoclonal antibodies, Francisella tularensis, binding site, tularemia, immunochemical characterization
NCBI PubMed ID: 22747335Publication DOI: 10.1021/bi201711mJournal NLM ID: 0370623Publisher: American Chemical Society
Correspondence: seatonba@bu.edu
Institutions: Department of Physiology and Biophysics and double daggerDepartment of Pathology and Laboratory Medicine, Boston University School of Medicine, Boston, Massachusetts 02118, United States
Methods: X-ray, DNA techniques, RT-PCR
- Article ID: 4477
Andres D, Gohlke U, Broeker NK, Schulze S, Rabsch W, Heinemann U, Barbirz S, Seckler R "An essential serotype recognition pocket on phage P22 tailspike protein forces Salmonella enterica serovar Paratyphi A O-antigen fragments to bind as non-solution conformers" -
Glycobiology 23(4) (2013) 486-494
Bacteriophage P22 recognizes O-antigen polysaccharides of Salmonella enterica subsp. enterica (S.) with its tailspike protein (TSP). In the serovars S. Typhimurium, S. Enteritidis, and S. Paratyphi A, the tetrasaccharide repeat units of the respective O-antigens consist of an identical main chain trisaccharide but different 3,6-dideoxyhexose substituents. Here, the epimers abequose, tyvelose, and paratose determine the specific serotype. P22TSP recognizes O-antigen octasaccharides in an extended binding site with a single 3,6-dideoxyhexose binding pocket. We have isolated S. Paratyphi A octasaccharides which were not available previously and determined the crystal structure of their complex with P22TSP. We discuss our data together with crystal structures of complexes with S. Typhimurium and S. Enteritidis octasaccharides determined earlier. Isothermal titration calorimetry (ITC) showed that S. Paratyphi A octasaccharide binds P22TSP less tightly, with a difference in binding free energy of approximately 7 kJ/mol at 20 degrees C compared to S. Typhimurium and S. Enteritidis octasaccharides. Individual protein-carbohydrate contacts were probed by amino acid replacements showing that the dideoxyhexose pocket contributes to binding of all three serotypes. However, S. Paratyphi A octasaccharides bind in a conformation with an energetically unfavorable varphi / psi glycosidic bond angle combination. By contrast, octasaccharides from the other serotypes bind as solution-like conformers. Two water molecules are conserved in all P22TSP complexes with octasaccharides of different serotypes. They line the dideoxyhexose binding pocket and force the S. Paratyphi A octasaccharides to bind as non-solution conformers. This emphasizes the role of solvent as part of carbohydrate binding sites.
Salmonella enterica, paratose, bacterial O-antigen, carbohydrate interaction, structural thermodynamics, tailspike protein
NCBI PubMed ID: 23292517Publication DOI: 10.1093/glycob/cws224Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: seckler@uni-potsdam.de; barbirz@uni-potsdam.de
Institutions: Physikalische Biochemie, Universitat Potsdam, Karl-Liebknecht-Str. 24-25, 14476 Potsdam, Germany
Methods: crystallography, thermodynamics, statistical analysis, crystallization, surface plasmon resonance (SPR), ITC
- Article ID: 4568
Lu Z, Rynkiewicz MJ, Yang CY, Madico G, Perkins HM, Wang Q, Costello CE, Zaia J, Seaton BA, Sharon J "The binding sites of monoclonal antibodies to the nonreducing end of Francisella tularensis O-antigen accommodate mainly the terminal saccharide" -
Immunology 140(3) (2013) 374-389
We have previously described two types of protective B cell epitopes in the O-antigen (OAg) of the Gram negative bacterium Francisella tularensis: repeating internal epitopes targeted by the vast majority of anti-OAg monoclonal antibodies (mAbs), and a non-overlapping epitope at the nonreducing end targeted by the previously unique IgG2a mAb FB11. We now generated and characterized three mAbs specific for the nonreducing end of F. tularensis OAg, partially encoded by the same variable region germline genes, indicating that they target the same epitope. Like FB11, the new mAbs, Ab63 (IgG3), N213 (IgG3), and N62 (IgG2b), had higher antigen-binding bivalent avidity than internal-binding anti-OAg mAbs, and an oligosaccharide containing a single OAg repeat was sufficient for optimal inhibition of their antigen-binding. The X-ray crystal structure of N62 Fab showed that the antigen-binding site is lined mainly by aromatic amino acids that form a small cavity, which can accommodate no more than one and a third sugar residues, indicating that N62 binds mainly to the terminal Qui4NFm residue at the nonreducing end of OAg. In efficacy studies with mice infected intranasally with the highly virulent F. tularensis strain SchuS4, N62, N213 and Ab63 prolonged survival and reduced blood bacterial burden. These results yield insights into how antibodies to nonreducing ends of microbial polysaccharides can contribute to immune protection despite the smaller size of their target epitopes compared with antibodies to internal polysaccharide regions.
epitopes, vaccines, immunoglobulins, bacteria/bacterial immunity, endotoxin/lipopolysaccharide
NCBI PubMed ID: 23844703Publication DOI: 10.1111/imm.12150Journal NLM ID: 0374672Publisher: Oxford, UK: Blackwell Scientific Publications
Correspondence: jsharon@bu.edu
Institutions: Department of Pathology and Laboratory Medicine, Boston University School of Medicine, Boston, MA, USA
Methods: X-ray, ELISA, Western blotting, biological assays, serological methods
- Article ID: 4683
Hong Y, Reeves PR "Diversity of O-antigen repeat unit structures can account for the substantial sequence variation of Wzx translocases" -
Journal of Bacteriology 196(9) (2014) 1713-1722
The most common system for synthesis of cell surface polysaccharides is the Wzx/Wzy-dependent pathway, which involves synthesis, on the cytoplasmic face of the cell membrane, of repeat units, which are then translocated to the periplasmic face by a Wzx translocase and then polymerized by Wzy to generate the polysaccharide. One such polysaccharide is O antigen, which is incorporated into lipopolysaccharide (LPS). The O antigen is extremely variable, with over 186 forms in Escherichia coli. Wzx proteins are also very diverse, but they have been thought to be specific only for the first sugar of the repeat units. However, recent studies demonstrated examples in which Wzx translocases have considerable preference for their native repeat unit, showing that specificity can extend well beyond the first sugar. These results appear to be in conflict with the early conclusions, but they involved specificity for side branch residues and could be a special case. Here we take six Wzx translocases that were critical in the earlier studies on the importance of the first sugar and assess their ability to translocate the Escherichia coli O16 and O111 repeat units. We use gene replacements to optimize maintenance of expression level and show that under these conditions the native translocases are the most effective for their native repeat unit, being, respectively, 64-fold and 4-fold more effective than the next best. We conclude that Wzx translocases are commonly adapted to their native repeat unit, which provides an explanation for the great diversity of wzx genes.
Lipopolysaccharide, structure, polysaccharide, O-antigen, Escherichia coli, specificity, Cell Membrane, membrane, surface polysaccharide, diversity
Publication DOI: 10.1128/JB.01323-13Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: peter.reeves@sydney.edu.au
Institutions: School of Molecular Bioscience (G08), University of Sydney, New South Wales, Australia
Methods: SDS-PAGE, genetic methods, cloning
- Article ID: 4703
Micoli F, Ravenscroft N, Cescutti P, Stefanetti G, Londero S, Rondini S, Maclennan CA "Structural analysis of O-polysaccharide chains extracted from different Salmonella Typhimurium strains" -
Carbohydrate Research 385 (2014) 1-8
Salmonella Typhimurium is the major cause of invasive nontyphoidal Salmonella disease in Africa, with high mortality among children and HIV-infected individuals. Currently, no vaccine is available for use in humans. Antibodies directed against the O-polysaccharide of the lipopolysaccharide molecule of Salmonella mediate bacterial killing and are protective, and conjugation of the O-polysaccharide to a carrier protein represents a possible strategy for vaccine development. Here we have purified the O-polysaccharide from six different strains of S. Typhimurium and fully characterized them using analytical methods including HPLC-SEC, HPAEC-PAD, GC, GC-MS, 1D and 2D NMR spectroscopy. All the O-polysaccharide samples showed a similar bimodal molecular mass distribution, but differed with respect to the amount and position of O-acetylation and glucosylation. For some strains, O-acetyl groups were found not only on C-2 of abequose (factor 5 specificity), but also on C-2 and C-3 of rhamnose; glucose was found to be linked 1→4 or 1→6 to galactose in different amounts according to the strain of origin. This structural variability could have an impact on the immunogenicity of corresponding glycoconjugate vaccines and different strains need to be evaluated in order to identify the appropriate source of O-polysaccharide to use for the development of a candidate conjugate vaccine with broad coverage against S. Typhimurium.
O-polysaccharide, bacterial polysaccharide structure, Salmonella typhimurium
NCBI PubMed ID: 24384528Publication DOI: 10.1016/j.carres.2013.12.003Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: francesca.micoli@novartis.com
Institutions: Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa, Novartis Vaccines Institute for Global Health, Via Fiorentina 1, I-53100 Siena, Italy, Dipartimento di Scienze della Vita, Ed. C11, Università di Trieste, via L. Giorgieri 1, 34127 Trieste, Italy, Medical Research Council Centre for Immune Regulation, Institute of Biomedical Research, School of Immunity and Infection, College of Medicine and Dental Sciences, University of Birmingham, Birmingham B15 2TT, UK
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, sugar analysis, acid hydrolysis, GLC, mild acid hydrolysis, de-O-acetylation, NMR-1D, HPLC, HPAEC-PAD, SEC
- Article ID: 4931
Kapaev RR, Toukach PV "Simulation of 2D NMR Spectra of Carbohydrates Using GODESS Software" -
Journal of Chemical Information and Modeling 55(6) (2016) 1100-1104
Glycan Optimized Dual Empirical Spectrum Simulation (GODESS) is a web service, which has been recently shown to be one of the most accurate tools for simulation of 1H and 13C 1D NMR spectra of natural carbohydrates and their derivatives. The new version of GODESS supports visualization of the simulated 1H and 13C chemical shifts in the form of most 2D spin correlation spectra commonly used in carbohydrate research, such as 1H-1H TOCSY, COSY/COSY-DQF/COSY-RCT, and 1H-13C edHSQC, HSQC-COSY, HSQC-TOCSY, and HMBC. Peaks in the simulated 2D spectra are color-coded and labeled according to the signal assignment and can be exported in JCAMP-DX format. Peak widths are estimated empirically from the structural features. GODESS is available free of charge via the Internet at the platform of the Carbohydrate Structure Database project ( http://csdb.glycoscience.ru ).
NMR, glycan, simulation, 2D NMR, HMBC, TOCSY, carbohydrate structure, Software, database, Glycan Optimized Dual Empirical Spectrum Simulation (GODESS), Internet, visualization
NCBI PubMed ID: 27227420Publication DOI: 10.1021/acs.jcim.6b00083Journal NLM ID: 101230060Publisher: Washington, D.C.: American Chemical Society
Correspondence: R.R.K
; P.V.T.
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow, Russia, Higher Chemical College of the Russian Academy of Sciences, Miusskaya sq. 9, Moscow, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, NMR-1D, simulation NMR-2D, GODESS
- Article ID: 4934
Hong Y, Reeves PR "Model for the Controlled Synthesis of O-Antigen Repeat Units Involving the WaaL Ligase" -
mSphere 1(1) (2016) e00074-15
The Wzx/Wzy O-antigen pathway involves synthesis of a repeat unit (O unit) consisting of 3 to 8 sugars on an inner-membrane-embedded lipid carrier. These O units are translocated across the membrane to its periplasmic face by Wzx, while retaining linkage to the carrier, and then polymerized by Wzy to O-antigen polymer, which WaaL ligase transfers to a lipopolysaccharide precursor to complete lipopolysaccharide synthesis, concomitantly releasing the lipid carrier. This lipid carrier is also used for peptidoglycan assembly, and sequestration is known to be toxic. Thus, O-unit synthesis must involve precise regulation to meet demand but avoid overproduction. Here we show that loss of WaaL reverses a known growth defect in a Salmonella mutant that otherwise accumulates O-unit intermediates and propose that WaaL is also involved in a novel feedback mechanism to regulate O-unit synthesis, based on the availability of O units on the periplasmic face of the membrane.
Lipopolysaccharide, O-antigen, molecular, Salmonella, wzx, wzy, WaaL ligase
Publication DOI: 10.1128/mSphere.00074-15Journal NLM ID: 101674533Publisher: Washington, DC: American Society for Microbiology
Correspondence: Peter R. Reeves
Institutions: School of Molecular Bioscience (D17), The University of Sydney, New South Wales, Australia
Methods: SDS-PAGE, genetic methods
- Article ID: 5094
Li P, Liu Q, Luo H, Liang K, Yi J, Luo Y, Hu Y, Han Y, Kong Q "O-Serotype Conversion in Salmonella Typhimurium Induces Protective Immune Responses against Invasive Non-Typhoidal Salmonella Infections" -
Frontiers in Immunology 8 (2017) 1647
Salmonella infections remain a big problem worldwide, causing enteric fever by Salmonella Typhi (or Paratyphi) or self-limiting gastroenteritis by non-typhoidal Salmonella (NTS) in healthy individuals. NTS may become invasive and cause septicemia in elderly or immuno-compromised individuals, leading to high mortality and morbidity. No vaccines are currently available for preventing NTS infection in human. As these invasive NTS are restricted to several O-antigen serogroups including B1, D1, C1, and C2, O-antigen polysaccharide is believed to be a good target for vaccine development. In this study, a strategy of O-serotype conversion was investigated to develop live attenuated S. Typhimurium vaccines against the major serovars of NTS infections. The immunodominant O4 serotype of S. Typhimurium was converted into O9, O7, and O8 serotypes through unmarked chromosomal deletion-insertion mutations. O-serotype conversion was confirmed by LPS silver staining and western blotting. All O-serotype conversion mutations were successfully introduced into the live attenuated S. Typhimurium vaccine S738 (Δcrp Δcya) to evaluate their immunogenicity in mice model. The vaccine candidates induced high amounts of heterologous O-polysaccharide-specific functional IgG responses. Vaccinated mice survived a challenge of 100 times the 50% lethality dose (LD50) of wild-type S. Typhimurium. Protective efficacy against heterologous virulent Salmonella challenges was highly O-serotype related. Furthermore, broad-spectrum protection against S. Typhimurium, S. Enteritidis, and S. Choleraesuis was observed by co-vaccination of O9 and O7 O-serotype-converted vaccine candidates. This study highlights the strategy of expressing heterologous O-polysaccharides via genetic engineering in developing live attenuated S. Typhimurium vaccines against NTS infections.
O-antigen, cross-protection, S. Choleraesuis, S. Enteritidis, S. Newport, S. Typhimurium, live attenuated Salmonella vaccine
NCBI PubMed ID: 29255460Publication DOI: 10.3389/fimmu.2017.01647Journal NLM ID: 101560960Publisher: Lausanne: Frontiers Research Foundation
Correspondence: kongqiki@163.com
Institutions: Institute of Preventive Veterinary Medicine, College of Veterinary Medicine, Sichuan Agricultural University, Chengdu, China, Center for Infectious Diseases and Vaccinology, The Biodesign Institute, Arizona State University, Tempe, AZ, United States, College of Animal Science and Technology, Southwest University, Chongqing, China, Department of Infectious Diseases and Pathology, University of Florida, Gainesville, FL, United States
Methods: SDS-PAGE, DNA techniques, ELISA, Western blotting, biological assays, serological methods, genetic methods, statistical analysis, motility assays
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2. Compound ID: 277
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a-Abep2Ac-(1-3)-+ a-D-Glcp-(1-4)-+
| |
-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_135513,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_137486,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_153307,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 73
Feldman MF, Marolda CL, Monteiro MA, Perry MB, Parodi AJ, Valvano MA "The activity of a putative polyisoprenol-linked sugar translocase (Wzx) involved in Escherichia coli O antigen assembly is independent of the chemical structure of the O repeat" -
Journal of Biological Chemistry 274(49) (1999) 35129-35138
During O antigen lipopolysaccharide (LPS) synthesis in bacteria, transmembrane migration of undecaprenylpyrophosphate (Und-P-P)-bound O antigen subunits occurs before their polymerization and ligation to the rest of the LPS molecule. Despite the general nature of the translocation process, putative O-antigen translocases display a low level of amino acid sequence similarity. In this work, we investigated whether complete O antigen subunits are required for translocation. We demonstrate that a single sugar, GlcNAc, can be incorporated to LPS of Escherichia coli K-12. This incorporation required the functions of two O antigen synthesis genes, wecA (UDP-GlcNAc:Und-P GlcNAc-1-P transferase) and wzx (O-antigen translocase). Complementation experiments with putative O-antigen translocases from E. coli O7 and Salmonella enterica indicated that translocation of O antigen subunits is independent of the chemical structure of the saccharide moiety. Furthermore, complementation with putative translocases involved in synthesis of exopolysaccharides demonstrated that these proteins could not participate in O antigen assembly. Our data indicate that recognition of a complete Und-P-P-bound O antigen subunit is not required for translocation and suggest a model for O antigen synthesis involving recognition of Und-P-P-linked sugars by a putative complex made of Wzx translocase and other proteins involved in the processing of O antigen
biosynthesis, antigen, structure, O-antigen, O antigen, Escherichia, Escherichia coli, activity, assembly, chemical, chemical structure, putative, sugar
NCBI PubMed ID: 10574995Publication DOI: 10.1074/jbc.274.49.35129Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: mvalvano@julian.uwo.ca
Institutions: Instituto de Investigaciones Bioquimicas Fundacion Campomar, Buenos Aires, Argentina, Department of Microbiology and Immunology, University of Western Ontario, London, Ontario N6A 5C1, Canada, Institute for Biological Sciences, National Research Council, Ottawa, Ontario K1A 0R6, Canada
- Article ID: 310
Liu D, Lindqvist L, Reeves PR "Transferases of O-antigen biosynthesis in Salmonella enterica: Dideoxyhexosyltransferases of groups B and C2 and acetyltransferase of group C2" -
Journal of Bacteriology 177(14) (1995) 4084-4088
The O antigen is a polymer of oligosaccharide units. O antigens differ in their sugar composition and glycosidic linkages, and genes responsible for O-antigen-specific biosynthesis are grouped in the rfb gene cluster. In this study, we identified two abequosyltransferase genes and an acetyltransferase gene in Salmonella enterica groups B and C2 by in vitro assay and identified paratosyl-, tyvelosyl-, and abequosyltransferase genes from S. enterica groups A and D and Yersinia pseudotuberculosis serovar IIA, respectively, by comparison.
biosynthesis, O-antigen, transferase, Salmonella, Salmonella enterica, 3, 6-dideoxyhexose, acetyltransferase
NCBI PubMed ID: 7541787Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: reeves@angis.su.oz.au
Institutions: Department of Microbiology, University of Sydney, New South Wales 2006, Australia, and Department of Clinical Bacteriology, Huddinge Hospital, Karolinska Institute, S-141 86 Huddinge, Sweden.
- Article ID: 3615
Bastin DA, Stevenson G, Brown PK, Haase A, Reeves PR "Repeat unit polysaccharides of bacteria. A model for polymerization resembling that of ribosomes and fatty acid synthetase, with a novel mechanism for determining chain length" -
Molecular Microbiology 7(5) (1993) 725-734
We report the identification and sequence from Escherichia coli and Salmonella enterica strains of the cld gene, encoding the chain-length determinant (CLD) which confers a modal distribution of chain length on the O-antigen component of lipopolysaccharide (LPS). The distribution of chain lengths in the absence of this gene fits a model in which as the chain is extended there is a constant probability of 0.165 of transfer of growing chain to LPS core, with termination of chain extension. The data for E. coli 0111 fit a model in which the CLD reduces this probability for short chains and increases it to 0.4 for longer chains, leading to a reduced number of short chain molecules but an increase in numbers of longer molecules and transfer of essentially all molecules by chain length 21. We put forward a model for O-antigen polymerase which resembles the ribosome and fatty acid synthetase in having two sites, with the growing chain being transferred from a D site onto the new unit at the R site to extend the chain and then back to the D site to repeat the process. It is proposed that the CLD protein and polymerase form a complex which has two states:'E'facilitating extension and T facilitating transfer to core. The complex is postulated to enter the E state as O-antigen polymerization starts, and to shift to the T state after a predetermined time, the CLD acting as a molecular clock. The CLD is not O-antigen or species-specific but the modal value does depend on the source of the cld gene.
biosynthesis, transfer, gene, O-antigen, repeating unit, Salmonella enterica, sequence, synthetase
NCBI PubMed ID: 7682279Journal NLM ID: 8712028Publisher: Blackwell Publishing
Institutions: Department of Microbiology, University of Sydney, Sydney, NSW 2006, Australia
Methods: genetic methods
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3. Compound ID: 928
|
?%a-Kdop-(2-4)-+
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EtN-(1-0)-?%P-7)-a-Kdop-(2-4)-+
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EtN-(1-0)-?%P-0)-?%P-4)-+ |
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L-gro-a-D-manHepp-(1-7)-+ | |
| | |
a-D-GlcpNAc-(1-2)-+ | | |
| | | |
Subst-(1-2)-+ a-D-Glcp-(1-4)-+ | a-D-Galp-(1-6)-+ | | |
| | | | | | |
a-Abep2Ac-(1-3)-a-D-Manp-(1-4)-b-L-Rhap-(1-3)-a-D-Galp-(1-4)-a-D-Glcp-(1-2)-a-D-Galp-(1-3)-a-D-Glcp-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
|
?%P-4)-+
Subst = O-antigen |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide with O-unit
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130656,IEDB_130659,IEDB_130670,IEDB_130693,IEDB_130701,IEDB_133751,IEDB_135513,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_140088,IEDB_140529,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_150901,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_153307,IEDB_190606,IEDB_2189047,IEDB_225177,IEDB_226811,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 266
Inagaki M, Kawaura T, Wakashima H, Kato M, Nishikawa S, Kashimura N "Different contributions of the outer and inner R-core residues of lipopolysaccharide to the recognition by spike H and G proteins of bacteriophage phiX174" -
FEMS Microbiology Letters 226(2) (2003) 221-227
The binding of spike H and G proteins of bacteriophage phiX174 with lipopolysaccharides (LPSs) were evaluated by a competitive enzyme-linked plate assay using the biotin-labeled LPS of Escherichia coli C, one of a host strain, and the non-labeled LPSs having different R-core polysaccharide lengths. H protein promptly decreased its affinity when some saccharide residues were truncated from the outer R-core. However, G protein showed significant affinity to the LPSs lacking all the residues of the outer R-core and some of the inner R-core. Thus, G protein rather than H protein well recognized the residues of the inner R-core of LPS
LPS, core, bacteriophage, proteins, G-protein, phiX174, host recognition, spike protein
NCBI PubMed ID: 14553915Journal NLM ID: 7705721Publisher: Blackwell Publishing
Correspondence: inagaki@bio.mie-u.ac.jp
Institutions: Department of Life Science, Faculty of Bioresources, Mie University, 1515 Kamihama, Tsu, 514-8507, Mie, Japan
Methods: DOC-PAGE, enzyme-linked plate assay
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4. Compound ID: 1060
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a-Abep2Ac-(1-3)-+ a-D-Glcp2Ac-(1-4)-+
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-4)-b-L-Rhap2Ac-(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_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_61,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 310
Liu D, Lindqvist L, Reeves PR "Transferases of O-antigen biosynthesis in Salmonella enterica: Dideoxyhexosyltransferases of groups B and C2 and acetyltransferase of group C2" -
Journal of Bacteriology 177(14) (1995) 4084-4088
The O antigen is a polymer of oligosaccharide units. O antigens differ in their sugar composition and glycosidic linkages, and genes responsible for O-antigen-specific biosynthesis are grouped in the rfb gene cluster. In this study, we identified two abequosyltransferase genes and an acetyltransferase gene in Salmonella enterica groups B and C2 by in vitro assay and identified paratosyl-, tyvelosyl-, and abequosyltransferase genes from S. enterica groups A and D and Yersinia pseudotuberculosis serovar IIA, respectively, by comparison.
biosynthesis, O-antigen, transferase, Salmonella, Salmonella enterica, 3, 6-dideoxyhexose, acetyltransferase
NCBI PubMed ID: 7541787Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: reeves@angis.su.oz.au
Institutions: Department of Microbiology, University of Sydney, New South Wales 2006, Australia, and Department of Clinical Bacteriology, Huddinge Hospital, Karolinska Institute, S-141 86 Huddinge, Sweden.
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5. Compound ID: 1132
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a-Abe-(1-3)-+ a-D-Glcp2Ac-(1-3)-+
| |
-4)-b-L-Rhap2Ac-(1-2)-b-D-Manp-(1-2)-a-D-Manp-(1-3)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Aglycon: core
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144995,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_164479,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_61,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 340
Nnalue NA, Lindberg AA "O-antigenic determinants in Salmonella species of serogroup C1 are expressed in distinct immunochemical populations of chains" -
Microbiology 143(2) (1997) 641-652
The O-antigenic specificities found among Salmonellae of serogroup C1 are O:6(1),7, O:6(2),7, O:6(1),6(2),7 and O:6,7,14, as defined by classical serology. Factor O:7 is the group-wide determinant while factors O:6(1), O:6(2) and O:14 are found in some strains but not others. Strains of the O:6(2),7 specificity are subject to lysogenic conversion by phages 6(1) and 14 to the O:6(1),7 and O:6,7,14 specificities, respectively. To further delineate antigenic complexity and serological relationships among strains of this serogroup monoclonal antibodies (mAbs) were generated against the O:6(1),6(2),7 polysaccharide of Salmonella thompson. Five mAbs of either the O:6(1) or O:6(2) specificities did not bind O:6,7,14 strains or LPS, showing that the O:6 determinant in these strains is neither O:6(1) nor O:6(2). Thus antigenic conversion of O:6(2),7 strains by phage 14 is accompanied by addition of O:14 as well as loss of O:6(2). Three mAbs which demonstrated group-wide reactivity, and were thus specific for O:7, recognized clearly by separable epitopes hereby defined as sub-specificities, O:7(1), O:7(2) and O:7(3). Immunoblotting of mAbs against electrophoretically resolved LPS showed that factors O:6(1) and O:6(2) are expressed only in LPS molecules of high molecular mass whereas O:7(2) and O:7(3) are expressed only in relatively low-molecular-mass chains. These results are consistent with the expression of different antigenic determinants in structurally distinct subpopulations of O chains. The implications of the existence of distinct subpopulation of chains is that the published structure of the O:6,7 repeat unit is not fully representative of the O-antigenic structure of this group
Salmonella LPS, LPS epitopes, O-antigenic complexity, O-antigen populations, antigenic conversionchain
NCBI PubMed ID: 9043141Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Institutions: Department of Medical Microbiology, Faculty of Medicine & Health Sciences, United Arab Emirates University, PO Box 17666, Al Ain, United Arab Emirates, Karolinska Institute, Department of Microbiology, Pathology and Infectious Diseases, Division of Clinical Bacteriology, Huddinge Hospital, S-14186, Huddinge, Sweden
Methods: SDS-PAGE, ELISA, immunoblotting
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6. Compound ID: 1137
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a-Abep-(1-3)-+
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a-D-Galp-(1-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-b-D-Galp-(1-1)-Me |
Show graphically |
Structure type: oligomer
Contained glycoepitopes: IEDB_127517,IEDB_130701,IEDB_135509,IEDB_135513,IEDB_136044,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_137486,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 344
Otter A, Hindsgaul O, Bundle DR "Gradient-enhanced homonuclear 2D NMR techniques applied to oligosaccharides containing manno-hexoses provide improved correlations for protons coupled by small 3J" -
Carbohydrate Research 275(2) (1995) 381-389
No abstract available
rhamnose, 2D NMR, Gradient-enhanced COSY, GCOSY, Gradient-enhanced double-quantum filtered COSY, GDQF-COSY, Gradient-enhanced TOCSY, GTOCSY, Spin-spin coupling, Small vicinal coupling constants, Mannose
NCBI PubMed ID: 8529230Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 262, Canada
Methods: NMR
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7. Compound ID: 1141
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a-Abep-(1-3)-b-D-6dmanHep-(1-4)-+
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-3)-a-D-Galp-(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_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,SB_173,SB_7
The structure is contained in the following publication(s):
- Article ID: 345
Pacinelli E, Wang L, Reeves PR "Relationship of Yersinia pseudotuberculosis O antigens IA, IIA, and IVB: the IIA gene cluster was derived from that of IVB" -
Infection and Immunity 70(6) (2002) 3271-3276
O antigen is part of the lipopolysaccharide present in the outer membrane of gram-negative bacteria and is highly polymorphic. In this study, we obtained sequences of the O-antigen gene clusters for the Yersinia pseudotuberculosis antigens IA, IIA, and IVB. We propose that the IIA gene cluster was derived from the IVB cluster, one of the very few cases in which a parent gene cluster is identified, and that the IA gene cluster could be a hybrid of the IVB and IB gene clusters. All three O antigens contain 6-deoxy-D-mannoheptose, and we identified six genes for the biosynthetic pathway for the precursor of this sugar, GDP-6-deoxy-D-mannoheptose
O-antigen, antigens, gene cluster, Yersinia pseudotuberculosis, relationship, Yersinia
NCBI PubMed ID: 12011023Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: Department of Microbiology, The University of Sydney, Sydney, New South Wales 2006, Australia
Methods: DNA sequencing
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8. Compound ID: 1228
Structure type: fragment of a bigger structure
Compound class: O-antigen
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_149558,IEDB_151528,IEDB_156494,IEDB_190606,IEDB_742246,IEDB_918313,IEDB_918314,SB_165,SB_166,SB_187,SB_195,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 381
Skurnik M, Zhang L "Molecular genetics and biochemistry of Yersinia lipopolysaccharide" -
APMIS: Acta Pathologica, Microbiologica, et Immunologica Scandinavica 104(12) (1996) 849-872
Studies on the molecular genetics of bacterial LPS serve at least two main purposes: (i) to help develop an understanding of the biology, biochemistry and genetics of this bacterial surface macromolecule, and (ii) to provide a basis for both vaccine development and virulence experiments. Both of these goals have been the driving force in studies of Yersinia LPS carried out during the last decade. Here we will review the progress made in the molecular genetics and biochemistry of Yersinia LPS. A deep understanding has been achieved with respect to Y. enterocolitica serotype O:3, reaching as far as a detailed analysis of the gene clusters directing the biosynthesis of the outer core oligosaccharide and of the O-ag. The O-ag gene clusters of Y. enterocolitica serotype O:8 and Y. pseudotuberculosis serotypes O:2a and O:5a have also been cloned and partially characterized LPS biosynthesis of these Yersinia species includes examples of the two major variations recognized in the biosynthesis of this macromolecule: (i) homopolymeric or O-antigen polymerase-independent biosynthesis, and (ii) heteropolymeric or O-antigen polymerase-dependent biosynthesis.
Lipopolysaccharide, genetic, gene, genetics, O-antigen, biochemistry, Yersinia, molecular genetics
NCBI PubMed ID: 9048864Publication DOI: 10.1111/j.1699-0463.1996.tb04951.xJournal NLM ID: 8803400Publisher: Copenhagen: Munksgaard
Institutions: Turku Centre for Biotechnology, University of Turku, Finland, department of Medical Microbiology, University of Turku, Turku, Finland
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9. Compound ID: 1231
Structure type: polymer chemical repeating unit
Compound class: O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_135513,IEDB_136045,IEDB_137485,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_152206,IEDB_152214,IEDB_174333,IEDB_983930,SB_44,SB_67,SB_72,SB_86
The structure is contained in the following publication(s):
- Article ID: 381
Skurnik M, Zhang L "Molecular genetics and biochemistry of Yersinia lipopolysaccharide" -
APMIS: Acta Pathologica, Microbiologica, et Immunologica Scandinavica 104(12) (1996) 849-872
Studies on the molecular genetics of bacterial LPS serve at least two main purposes: (i) to help develop an understanding of the biology, biochemistry and genetics of this bacterial surface macromolecule, and (ii) to provide a basis for both vaccine development and virulence experiments. Both of these goals have been the driving force in studies of Yersinia LPS carried out during the last decade. Here we will review the progress made in the molecular genetics and biochemistry of Yersinia LPS. A deep understanding has been achieved with respect to Y. enterocolitica serotype O:3, reaching as far as a detailed analysis of the gene clusters directing the biosynthesis of the outer core oligosaccharide and of the O-ag. The O-ag gene clusters of Y. enterocolitica serotype O:8 and Y. pseudotuberculosis serotypes O:2a and O:5a have also been cloned and partially characterized LPS biosynthesis of these Yersinia species includes examples of the two major variations recognized in the biosynthesis of this macromolecule: (i) homopolymeric or O-antigen polymerase-independent biosynthesis, and (ii) heteropolymeric or O-antigen polymerase-dependent biosynthesis.
Lipopolysaccharide, genetic, gene, genetics, O-antigen, biochemistry, Yersinia, molecular genetics
NCBI PubMed ID: 9048864Publication DOI: 10.1111/j.1699-0463.1996.tb04951.xJournal NLM ID: 8803400Publisher: Copenhagen: Munksgaard
Institutions: Turku Centre for Biotechnology, University of Turku, Finland, department of Medical Microbiology, University of Turku, Turku, Finland
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10. Compound ID: 1232
|
a-Abep-(1-6)-+
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-3)-a-D-GalpNAc-(1-3)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-b-D-Manp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_130701,IEDB_136104,IEDB_137473,IEDB_137485,IEDB_1391961,IEDB_140116,IEDB_141584,IEDB_141830,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_885822,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 381
Skurnik M, Zhang L "Molecular genetics and biochemistry of Yersinia lipopolysaccharide" -
APMIS: Acta Pathologica, Microbiologica, et Immunologica Scandinavica 104(12) (1996) 849-872
Studies on the molecular genetics of bacterial LPS serve at least two main purposes: (i) to help develop an understanding of the biology, biochemistry and genetics of this bacterial surface macromolecule, and (ii) to provide a basis for both vaccine development and virulence experiments. Both of these goals have been the driving force in studies of Yersinia LPS carried out during the last decade. Here we will review the progress made in the molecular genetics and biochemistry of Yersinia LPS. A deep understanding has been achieved with respect to Y. enterocolitica serotype O:3, reaching as far as a detailed analysis of the gene clusters directing the biosynthesis of the outer core oligosaccharide and of the O-ag. The O-ag gene clusters of Y. enterocolitica serotype O:8 and Y. pseudotuberculosis serotypes O:2a and O:5a have also been cloned and partially characterized LPS biosynthesis of these Yersinia species includes examples of the two major variations recognized in the biosynthesis of this macromolecule: (i) homopolymeric or O-antigen polymerase-independent biosynthesis, and (ii) heteropolymeric or O-antigen polymerase-dependent biosynthesis.
Lipopolysaccharide, genetic, gene, genetics, O-antigen, biochemistry, Yersinia, molecular genetics
NCBI PubMed ID: 9048864Publication DOI: 10.1111/j.1699-0463.1996.tb04951.xJournal NLM ID: 8803400Publisher: Copenhagen: Munksgaard
Institutions: Turku Centre for Biotechnology, University of Turku, Finland, department of Medical Microbiology, University of Turku, Turku, Finland
- Article ID: 1778
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 1882
Gorshkova RP, Isakov VV, Shevchenko LS, Ovodov YS "Structure of the O-specific polysaccharide chain of the lipopolysaccharide Yersinia pseudotuberculosis serovar II C" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 17(2) (1991) 252-257
An O-specific polysaccharide has been isolated on mild acid hydrolysis of lipopolysaccharide from Yersinia pseudotuberculosis serovar IIc and shown to consist of abequose, D-mannose and 2-acetamido-2-deoxy-D-galactose residues in the ratio 0.8:3:1. From the results of acid hydrolysis, 13C NMR, methylation and periodate oxidation studies the structure of the repeating unit of the O-specific polysaccharide is deduced as follows: (formula; see text).
NCBI PubMed ID: 1863285Journal NLM ID: 7804941Publisher: Moskva: Nauka
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok
Methods: 13C NMR
- Article ID: 2682
Ovodov YS, Gorshkova RP, Tomshich SV, Komandrova NA, Zubkov VA, Kalmykova EN, Isakov VV "Chemical and Immunochemical studies on lipopolysaccharides of some Yersinia species - A review of some recent investigations" -
Journal of Carbohydrate Chemistry 11 (1992) 21-35
The present paper revealed the results of some recent chemical and immunochemical studies of the lipopolysaccharides from various species and erologie variants of Yersinia genus as follows: Y. pseudotuberculosis IIC and VII; Y. enterocolitica 0:1, 2a, 3; 0:2a, 2b, 3; 0:3; 0:4, 32; 0:5; 0:5,27; 0:6,31; 0:7,8; 0:19,8; 0:8; Y. frederiksenii 0:16,29; Y. intermedia 0:4,33; Y. aldovae.
Publication DOI: 10.1080/07328309208016139Journal NLM ID: 8218151Publisher: Marcel Dekker
Institutions: The Pacific Institute of Bioorganic Chemistry, Far East Branch of the USSR Academy of Sciences, 690022, Vladivostok, U.S.S.R
Methods: 13C NMR, 1H NMR
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11. Compound ID: 1327
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a-Abep-(1-3)-+ a-D-Glcp-(1-6)-+
| |
-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_127517,IEDB_130701,IEDB_135509,IEDB_135513,IEDB_135514,IEDB_135611,IEDB_136093,IEDB_136105,IEDB_136775,IEDB_136906,IEDB_137472,IEDB_137486,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 414
Wang L, Andrianopoulos K, Liu D, Popoff MY, Reeves PR "Extensive variation in the O-antigen gene cluster within one Salmonella enterica serogroup reveals an unexpected complex history" -
Journal of Bacteriology 184(6) (2002) 1669-1677
The 46 serogroups of Salmonella enterica have different O-antigens, and each is thought to have a specific form of the O-antigen cluster. Comparison of the 145 serovars of serogroup B revealed much more intraserogroup genetic diversity than expected. The O27 factor, due to an α 1-6 linkage between O units in place of the more common α 1-2 linkage and previously thought to be due to a converting bacteriophage, is now shown to be due to a wzy(α(1-6)) gene located within the major gene cluster. Surprisingly a remnant of this gene in all O27(-) serovars shows that the ancestor was O27(+). There are six distinct gene cluster forms, five apparently derived by a series of deletions and one by an insertion from an ancestral O27(+) form present in 57 serovars. The history of the gene cluster and movement between subspecies I and II can be traced. Two of the derivative forms still have a functional wzy(α(1-6)) gene, while in three it has been inactivated by deletion or insertion. Two of the forms lacking a functional wzy(α(1-6)) gene have the wzy(α(1-2)) gene first described for strain LT2 as rfc, whereas for the third the wzy gene has not been located
variation, O-antigen, gene cluster, specific, Salmonella, insertion, Salmonella enterica, bacteriophage, serogroup B, genetic diversity, rfc
NCBI PubMed ID: 11872718Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: reeves@angis.org.au
Institutions: Department of Microbiology, The University of Sydney, Sydney, New South Wales 2006, Australia
Methods: DNA sequencing, SDS-PAGE
- Article ID: 1323
Zegelaar-Jaarsveld K, van der Plas SC, van der Marel GA, van Boom JH "Preparation of disaccharide haptens corresponding to Salmonella serogroups B and D" -
Journal of Carbohydrate Chemistry 15 (1996) 665-689
The properly protected ethyl 1-thio-abequopyranoside 11 and ethyl 1-thio-tyvelopyranoside 26 were prepared by a sequence of reactions, the key steps of which was the regioselective hydride-mediated ring-opening of the cyclic sulfate function in compound 8 and 18. Iodonium ion-assisted glycosylation of allyl mannopyranoside 30 with the individual ethyl 3,6-dideoxy-1-thio-D-hexopyranoside donors 11 and 26 furnished, after deprotection, the respective allyl 3-O-(a-D-abequopyranosyl)-a-D-mannopyranoside 1 and allyl 3-O-(a-D-tyvelopyranosyl)-a-D-mannopyranoside 2.
synthesis, oligosaccharide, polysaccharide, epitope, serogroup, Salmonella, hapten, disaccharide, abequose, tyvelose
Publication DOI: 10.1080/07328309608005684Journal NLM ID: 8218151Publisher: Marcel Dekker
Institutions: Leiden Institute of Chemistry, Gorlaeus Laboratoria, Leiden University, The Netherlands
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12. Compound ID: 1328
|
a-Abep-(1-3)-+ a-D-Glcp-(1-4)-+
| |
-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_127517,IEDB_130701,IEDB_135509,IEDB_135513,IEDB_135514,IEDB_135611,IEDB_136093,IEDB_136105,IEDB_136775,IEDB_136906,IEDB_137472,IEDB_137486,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 414
Wang L, Andrianopoulos K, Liu D, Popoff MY, Reeves PR "Extensive variation in the O-antigen gene cluster within one Salmonella enterica serogroup reveals an unexpected complex history" -
Journal of Bacteriology 184(6) (2002) 1669-1677
The 46 serogroups of Salmonella enterica have different O-antigens, and each is thought to have a specific form of the O-antigen cluster. Comparison of the 145 serovars of serogroup B revealed much more intraserogroup genetic diversity than expected. The O27 factor, due to an α 1-6 linkage between O units in place of the more common α 1-2 linkage and previously thought to be due to a converting bacteriophage, is now shown to be due to a wzy(α(1-6)) gene located within the major gene cluster. Surprisingly a remnant of this gene in all O27(-) serovars shows that the ancestor was O27(+). There are six distinct gene cluster forms, five apparently derived by a series of deletions and one by an insertion from an ancestral O27(+) form present in 57 serovars. The history of the gene cluster and movement between subspecies I and II can be traced. Two of the derivative forms still have a functional wzy(α(1-6)) gene, while in three it has been inactivated by deletion or insertion. Two of the forms lacking a functional wzy(α(1-6)) gene have the wzy(α(1-2)) gene first described for strain LT2 as rfc, whereas for the third the wzy gene has not been located
variation, O-antigen, gene cluster, specific, Salmonella, insertion, Salmonella enterica, bacteriophage, serogroup B, genetic diversity, rfc
NCBI PubMed ID: 11872718Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: reeves@angis.org.au
Institutions: Department of Microbiology, The University of Sydney, Sydney, New South Wales 2006, Australia
Methods: DNA sequencing, SDS-PAGE
- Article ID: 1260
Steinbacher S, Baxa U, Miller S, Weintraub A, Seckler R, Huber R "Crystal structure of phage P22 tailspike protein complexed with Salmonella sp O-antigen receptors" -
Proceedings of the National Academy of Sciences of the USA 93(20) (1996) 10584-10588
The O-antigenic repeating units of lipopolysaccharides from Salmonella serogroups A, B, and D1 serve as receptors for the phage P22 tailspike protein, which also has receptor destroying endoglycosidase (endorhamnosidase) activity, integrating the functions of both hemagglutinin and neuraminidase in influenza virus. Crystal structures of the tailspike protein in complex with oligosaccharides, comprising two O-antigenic repeating units from Salmonella typhimurium, Salmonella enteritidis, and Salmonella typhi 253Ty were determined at 1.8 A resolution. The active-site topology with Asp-392, Asp-395, and Glu-359 as catalytic residues was identified. Kinetics of binding and cleavage suggest a role of the receptor destroying endorhamnosidase activity primarily for detachment of newly assembled phages.
structure, O-antigen, Salmonella, crystal structure, endoglycosidase, hemagglutinin, phage, virus
NCBI PubMed ID: 8855221Journal NLM ID: 7505876Publisher: National Academy of Sciences
Institutions: Abteilung Strukturforschung, Max-Planck-Institut fur Biochemie, Martinsried, Germany, Physikalische Biochemie, Universitat Regensburg, Regensburg, Germany, Department of Immunology, Microbiology, Pathology and Infectious Diseases, Division of Clinical Bacteriology, Huddinge University Hospital, Karolinska Institutet, Huddinge, Sweden
Methods: X-ray
- Article ID: 1323
Zegelaar-Jaarsveld K, van der Plas SC, van der Marel GA, van Boom JH "Preparation of disaccharide haptens corresponding to Salmonella serogroups B and D" -
Journal of Carbohydrate Chemistry 15 (1996) 665-689
The properly protected ethyl 1-thio-abequopyranoside 11 and ethyl 1-thio-tyvelopyranoside 26 were prepared by a sequence of reactions, the key steps of which was the regioselective hydride-mediated ring-opening of the cyclic sulfate function in compound 8 and 18. Iodonium ion-assisted glycosylation of allyl mannopyranoside 30 with the individual ethyl 3,6-dideoxy-1-thio-D-hexopyranoside donors 11 and 26 furnished, after deprotection, the respective allyl 3-O-(a-D-abequopyranosyl)-a-D-mannopyranoside 1 and allyl 3-O-(a-D-tyvelopyranosyl)-a-D-mannopyranoside 2.
synthesis, oligosaccharide, polysaccharide, epitope, serogroup, Salmonella, hapten, disaccharide, abequose, tyvelose
Publication DOI: 10.1080/07328309608005684Journal NLM ID: 8218151Publisher: Marcel Dekker
Institutions: Leiden Institute of Chemistry, Gorlaeus Laboratoria, Leiden University, The Netherlands
- Article ID: 1485
Steinbacher S, Miller S, Baxa U, Weintraub A, Seckler R "Interaction of Salmonella phage P22 with its O-antigen receptor studied by X-ray crystallography" -
Biological Chemistry 378(3-4) (1997) 337-343
The O-antigenic repeating units of the Salmonella cell surface lipopolysaccharides (serotypes A, B and D1) serve as receptors for phage P22. This initial binding step is mediated by the tailspike protein (TSP), which is present in six copies on the base plate of the phage. In addition to the binding activity, TSP also displays a low endoglycolytic activity, cleaving the α(1,3)-O-glycosidic bond between rhamnose and galactose of the O-antigenic repeats. The crystal structure of TSP in complex with receptor fragments allowed to identify the receptor binding site for the octasaccharide product of the enzymatic action of TSP on delipidated LPS and the active site consisting of Asp392, Asp395 and Glu359. The structure comprises a large right-handed parallel beta-helix of 13 turns. These fold independently in the trimer, whereas the N-terminus forms a cap-like structure and the C-terminal parts of the three polypeptide strands merge to a single common domain. In addition, TSP has served as model system for the folding of large, multisubunit proteins. Its folding pathway is influenced by a large number of point mutations, classified as lethal, temperature sensitive or general suppressor mutations, which influence the partitioning between aggregation and the productive folding pathway.
O-antigen, Salmonella, crystal structure, endoglycosidase, X-ray crystallography, phage mutants, protein folding, receptor binding, β-helix, virus proyein
NCBI PubMed ID: 9165091Journal NLM ID: 9700112Publisher: Berlin: Walter De Gruyter
Institutions: Max-Planck-Institut für Biochemie, Abteilung für Strukturforschung, Martinsried, Germany, Institut für Biophysik und Physikalische Biochemie, Universitat Regensburg, D-93040 Regensburg, Germany, Department of Immunology, Pathology and Infectious Diseases Division of Clinical Bacteriology, Huddinge University Hospital, Karolinska Institutet, Huddinge, Sweden
Methods: X-ray
- Article ID: 1778
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 3153
Szafranek J, Kumirska J, Czerwicka M, Kunikowska D, Dziadziuszko H, Glosnicka R "Structure and heterogeneity of the O-antigen chain of Salmonella agona lipopolysaccharide" -
FEMS Immunology and Medical Microbiology 48(2) (2006) 223-236
Lipopolysaccharide of Salmonella Agona smooth-type cells was obtained from bacteria by a hot phenol-water extraction procedure. Mild acid hydrolysis of lipopolysaccharide, followed by gel filtration, yielded the pure O-polysaccharide. Abequose, rhamnose, mannose, galactose and glucose in the molar ratio 0.8 : 1.0 : 1.0 : 1.1 : 0.5 were detected, and their linkages were established. Sugar configurations were determined by gas chromatography. Two repeating units, namely →2)-[α-Abep-(1→3)-]-α-D-Manp-(1→4)-α-L-Rhap-(1→3)-α-D-Galp-(1→ and →2)-[α-Abep-(1→3)-]-α-D-Manp-(1→4)-α-L-Rhap-(1→3)-[α-D-Glcp-(1→4)-]-α-D-Galp-(1→, were deduced from nuclear magnetic resonance studies. The effort to separate them was unsuccessful. An immunochemical test performed by means of Western blotting with anti O12 serum demonstrated that glucose was present in the longer lipopolysaccharide chains, at some distance from the core region.
Lipopolysaccharide, structure, O-antigen, O antigen, chain, Salmonella, heterogeneity, D
NCBI PubMed ID: 17064278Journal NLM ID: 9315554Publisher: Elsevier
Correspondence: janat@chem.univ.gda.pl
Institutions: Department of Chemistry, University of Gdansk, Gdansk, Poland
Methods: GC, composition analysis
- Article ID: 3578
Kaczyński Z, Gajdus J, Dziadziuszko H, Stepnowski P "Chemical structure of the somatic antigen isolated from Salmonella Abortusequi (O4)" -
Journal of Pharmaceutical and Biomedical Analysis 50(4) (2009) 679-682
A neutral O-specific polysaccharide was obtained by mild acid hydrolysis of the lipopolysaccharide (LPS) of Salmonella Abortusequi O4 bacterium (previously serogroup B). As determined by compositional analyses and NMR spectroscopy, the O-polysaccharide consists of four or five residues in the repeating subunit. The assigned structures are: and A distribution of the repeating units in O-chain was analysed by Western blotting with anti O12 serum and MS spectrometry of oligosaccharides obtained from partial hydrolysis of polysaccharide
NMR, structure, O-polysaccharide, Salmonella abortusequi
NCBI PubMed ID: 19058946Publication DOI: 10.1016/j.jpba.2008.10.013Journal NLM ID: 8309336Publisher: London: Elsevier
Correspondence: Z. Kaczyński
Institutions: Faculty of Chemistry, University of Gdansk, Gdansk, Poland
Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, FAB-MS, partial acid hydrolysis, SDS-PAGE, sugar analysis, GLC, Western blotting, composition analysis, NMR-1D, immunoblotting
- Article ID: 6047
Di Benedetto R, Alfini R, Carducci M, Aruta MG, Lanzilao L, Acquaviva A, Palmieri E, Giannelli C, Necchi F, Saul A, Micoli F "Novel Simple Conjugation Chemistries for Decoration of GMMA with Heterologous Antigens" -
International Journal of Molecular Sciences 22(19) (2021) 10180
Outer Membrane Vesicles (OMV) constitute a promising platform for the development of efficient vaccines. OMV can be decorated with heterologous antigens (proteins or polysaccharides), becoming attractive novel carriers for the development of multicomponent vaccines. Chemical conjugation represents a tool for linking antigens, also from phylogenetically distant pathogens, to OMV. Here we develop two simple and widely applicable conjugation chemistries targeting proteins or lipopolysaccharides on the surface of Generalized Modules for Membrane Antigens (GMMA), OMV spontaneously released from Gram-negative bacteria mutated to increase vesicle yield and reduce potential reactogenicity. A Design of Experiment approach was used to identify optimal conditions for GMMA activation before conjugation, resulting in consistent processes and ensuring conjugation efficiency. Conjugates produced by both chemistries induced strong humoral response against the heterologous antigen and GMMA. Additionally, the use of the two orthogonal chemistries allowed to control the linkage of two different antigens on the same GMMA particle. This work supports the further advancement of this novel platform with great potential for the design of effective vaccines.
vaccine, glycoconjugate, GMMA, carrier protein, conjugation chemistry, OVM
NCBI PubMed ID: 34638530Publication DOI: 10.3390/ijms221910180Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: francesca.x.micoli@gsk.com
Institutions: GSK Vaccines Institute for Global Health (GVGH), Via Fiorentina 1, 53100 Siena, Italy
Methods: periodate oxidation, SDS-PAGE, ELISA, Western blotting, immunization, conjugation, HPLC-SEC, reductive amination
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13. Compound ID: 1329
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a-Abep-(1-3)-+
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-6)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_135513,IEDB_136093,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_137486,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 414
Wang L, Andrianopoulos K, Liu D, Popoff MY, Reeves PR "Extensive variation in the O-antigen gene cluster within one Salmonella enterica serogroup reveals an unexpected complex history" -
Journal of Bacteriology 184(6) (2002) 1669-1677
The 46 serogroups of Salmonella enterica have different O-antigens, and each is thought to have a specific form of the O-antigen cluster. Comparison of the 145 serovars of serogroup B revealed much more intraserogroup genetic diversity than expected. The O27 factor, due to an α 1-6 linkage between O units in place of the more common α 1-2 linkage and previously thought to be due to a converting bacteriophage, is now shown to be due to a wzy(α(1-6)) gene located within the major gene cluster. Surprisingly a remnant of this gene in all O27(-) serovars shows that the ancestor was O27(+). There are six distinct gene cluster forms, five apparently derived by a series of deletions and one by an insertion from an ancestral O27(+) form present in 57 serovars. The history of the gene cluster and movement between subspecies I and II can be traced. Two of the derivative forms still have a functional wzy(α(1-6)) gene, while in three it has been inactivated by deletion or insertion. Two of the forms lacking a functional wzy(α(1-6)) gene have the wzy(α(1-2)) gene first described for strain LT2 as rfc, whereas for the third the wzy gene has not been located
variation, O-antigen, gene cluster, specific, Salmonella, insertion, Salmonella enterica, bacteriophage, serogroup B, genetic diversity, rfc
NCBI PubMed ID: 11872718Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: reeves@angis.org.au
Institutions: Department of Microbiology, The University of Sydney, Sydney, New South Wales 2006, Australia
Methods: DNA sequencing, SDS-PAGE
- Article ID: 1408
Curd H, Liu D, Reeves PR "Relationships among the O-antigen gene clusters of Salmonella enterica groups B, D1, D2, and D3" -
Journal of Bacteriology 180(4) (1998) 1002-1007
The O antigen is an important cell wall antigen of gram-negative bacteria, and the genes responsible for its biosynthesis are located in a gene cluster. We have cloned and sequenced the DNA segment unique to the O-antigen gene cluster of Salmonella enterica group D3. This segment includes a novel O-antigen polymerase gene (wzyD3). The polymerase gives α(1→6) linkages but has no detectable sequence similarity to that of group D2, which confers the same linkage. We find the remnant of a D3-like wzy gene in the O-antigen gene clusters of groups D1 and B and suggest that this is the original wzy gene of these O-antigen gene clusters.
gene, O-antigen, O antigen, group, cluster, gene cluster, Salmonella, Salmonella enterica, relationship
NCBI PubMed ID: 9473060Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: reeves@angis.usyd.edu.au
Institutions: Department of Microbiology, The University of Sydney,Australia
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14. Compound ID: 2543
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a-Abep4Ac-(1-3)-+ a-D-Glcp-(1-2)-+
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-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: 866
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: 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: 3707
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, methylation, GLC-MS, NMR-2D, SDS-PAGE, sugar analysis, acid hydrolysis, serological 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
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15. Compound ID: 2544
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a-Abep-(1-3)-+
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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: 866
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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