Found 29 structures.
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1. Compound ID: 275
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a-Abep2Ac-(1-3)-+ a-D-Glcp-(1-4)-+
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-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: 72
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: 309
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: 3614
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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2. Compound ID: 926
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?%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)-+ | |
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a-D-GlcpNAc-(1-2)-+ | | |
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Subst-(1-2)-+ a-D-Glcp-(1-4)-+ | a-D-Galp-(1-6)-+ | | |
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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/
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?%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_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: 265
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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3. Compound ID: 3963
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a-D-Glcp-(1-3)-+
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a-Abep2Ac-(1-3)-+ |
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-2)-a-D-Manp-(1-2)-b-D-Manp-(1-2)-b-D-Manp-(1-2)-b-D-Manp-(1-3)-a-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_133966,IEDB_133967,IEDB_134618,IEDB_135513,IEDB_136104,IEDB_137485,IEDB_140116,IEDB_141807,IEDB_142488,IEDB_144983,IEDB_144995,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_152206,IEDB_153307,IEDB_1539315,IEDB_858578,IEDB_983930,IEDB_983931,SB_136,SB_192,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 1467
Knirel YA, Kocharova NA, Bystrova OV, Katzenellenbogen E, Gamian A "Structures and serology of the O-specific polysaccharides of bacteria of the genus Citrobacter" -
Archivum Immunologiae et Therapiae Experimentalis 50(6) (2002) 379-391
The review presents the structures of the O-specific polysaccharides (O-antigens) of the lipopolysaccharides isolated from over 25 Citrobacter strains, which represent different species and serogroups. The correlation between O-antigen structure and immunospecificity as well as numerous cross-reactions between Citrobacter and other enterobacterial species are discussed.
Lipopolysaccharide, structure, O-antigen, O-specific polysaccharide, serology, Citrobacter, immunospecificity
NCBI PubMed ID: 12546064Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 3706
Katzenellenbogen E, Kocharova NA, Toukach FV, Gorska S, Korzeniowska-Kowal A, Bogulska M, Gamian A, Knirel YA "Structure of an abequose-containing O-polysaccharide from Citrobacter freundii O22 strain PCM 1555" -
Carbohydrate Research 344(13) (2009) 1724-1728
The lipopolysaccharide of Citrobacter freundii O22 (strain PCM 1555) was degraded under mild acidic conditions and the O-polysaccharide released was isolated by gel chromatography. Sugar and methylation analyses along with 1H and 13C NMR spectroscopy, including two-dimensional 1H,1H ROESY and 1H,13C HMBC experiments, showed that the repeating unit of the O-polysaccharide has the following structure: where Abe is abequose (3,6-dideoxy-d-xylo-hexose). SDS-PAGE and immunoblotting revealed that the O-antigen of C. freundii O22 is serologically indistinguishable from those of Salmonella group B serovars (Typhimurium, Brandenburg, Sandiego, Paratyphi B) but not related to other abequose-containing O-antigens tested (Citrobacter werkmanii O38 and Salmonella Kentucky) or colitose (l enantiomer of abequose)-containing O-antigen of Escherichia coli O111.
Lipopolysaccharide, endotoxin, O-Specific polysaccharide structure, serological classification, Citrobacter, Citrobacter freundii
NCBI PubMed ID: 19576576Publication DOI: 10.1016/j.carres.2009.06.005Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: katzenel@iitd.pan.wroc.pl (E. Katzenellenbogen)
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation, L.Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wrocław, Poland, Department of Medical Biochemistry, Wrocław Medical University, Wrocław, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, SDS-PAGE, sugar analysis, acid hydrolysis, serological methods
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4. Compound ID: 4678
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a-Abep2Ac-(1-3)-+ a-D-Glcp-(1-6)-+
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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: 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_153307,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: 1673
Whitfield C, Valvano MA "Biosynthesis and expression of cell-surface polysaccharides in gram-negative bacteria" -
Advances in Microbial Physiology 35 (1993) 135-246
This chapter provides an overview of the molecular mechanisms involved in synthesis and expression of cell-surface polysaccharides in Gram-negative bacteria. Biosynthesis of many cell-surface components, including polysaccharides, involves enzymes and enzyme complexes found in the cytoplasmic membrane. The peptidoglycan layer is located immediately external to the cytoplasmic membrane and this layer is required for cell shape and rigidity. Gram-negative bacteria possess a periplasm that contains a variety of proteins and enzymes, including some involved in import and export of macromolecules. Biosynthesis of bacterial cell-surface polysaccharides involves a series of sequential processes: (1) biosynthesis of activated precursors in the cytoplasm, (2) formation of repeating units, (3) polymerization of repeating units, and (d) export of polysaccharides to the cell surface. The assembly of polysaccharide repeating units and subsequent polymerization reactions occur at the cytoplasmic membrane, using precursors synthesized in the cytoplasm. Genes for biosynthesis of cell-surface polysaccharides are chromosomal and are arranged in clusters of one or more transcriptional units. The synthesis of lipopolysaccharide (LPS) may be subject to complex regulation, but on-off switching is not possible due to the essential structural requirement for the lipid A-core LPS molecule. Most bacteria use extracellular polysaccharides (EPSs) for protection, and many regulatory strategies are directed to modulating EPS synthesis in response to appropriate environmental cues. Application of genetic and biochemical approaches has facilitated detailed analysis of complex, multicomponent systems, such as those involved in synthesis of cell-surface polysaccharides.
NCBI PubMed ID: 8310880Publication DOI: 10.1016/S0065-2911(08)60099-5Journal NLM ID: 0117147Institutions: Department of Microbiology, University of Guelph, Ontario, Canada, Department of Microbiology, University of Guelph, Guelph, Ontario, Canada, Department of Microbiology and Immunology, University of Western Ontario, London, Ontario, Canada, N6A 5C1
- Article ID: 1777
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: 3846
Gajdus J, Glosnicka R, Szafranek J "Primary structure of Salmonella spp. O-antigens" -
Wiadomosci Chemiczne [Polish] 60(9-10) (2006) 621-653
Salmonella spp. are pathogenic Gram-negative bacteria that belong to Enterobacteriaceae family with lipopolysaccharide (LPS) as a constituent of cell wall. This is an integral component of the outer membrane of the wall. Salmonella smooth (S) forms produce LPS, which is composed of three parts, chemically bonded together viz. polysaccharide O-antigen, oligosaccharide core region and lipid A. Antigens O (O-PS) together with H flagella antigens are the foundation of serological classification of these bacteria. O-chain, which is built with up to 50 oligosaccharide repeating units, is one of the products of mild acidic hydrolysis of LPS. Due to the fact that polysaccharide antigens are the sites of specific antibody complexing, any difference in primary and secondary structures of O-antigens reflect serological specificity of bacteria. Taking this fact into consideration, we can distinguish about 2541 Salmonella serotypes with O and H antigenic formulas defined [4]. In this review we present 55 chemical structures of O-antigenic repeating units of Salmonella strains including their heterogeneity structures. The structures can have 22 different monosaccharide residues usually in 3 to 6 sugar repeating units. We describe here selected chemical and spectroscopic (MS, NMR) methods for primary structure examination of these bacterial O-PS. Enzymatic and immunochemical methods are also described. Cross-reactions of Salmonella spp. with any other bacteria or blood group A, B, 0 antigens are explained on the molecular level. Thus, structural assignments of somatic antigens of Salmonella spp. allow us to understand the molecular level of the classification system of these bacteria.
NMR spectroscopy, O-antigens, Salmonella, MS, primary structure
WWW link: http://baztech.icm.edu.pl/baztech/cgi-bin/btgetdoc.cgi?BUS2-0016-0014Publisher: Polish Chemical Society
Correspondence: jerzyg@chemik.chem.univ.gda.pl
Institutions: Wydzial Chemii, Uniwersytet Gdanski, ul. Sobieskiego 18, 80-952 Gdansk
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5. Compound ID: 5759
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a-Abep2Ac-(1-3)-+
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a-Abep-(1-3)-+ a-D-Glcp-(1-4)-+ | a-D-Glcp-(1-6)-+
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-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1-2)-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_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_153307,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: 2515
Pokrovskii VV, Tregub AV, Tendetnik YY, Pokrovskii VI, Kochetkov NK, Chernyak AY, Levinskii AB "Immunobiological properties of synthetic antigen copolymers of synthetic O-determinants with acrylamide" -
Soviet Immunology = Immunologiya (1986) 46-50
Journal NLM ID: 8406555Publisher: New York, NY: Allerton Press
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6. Compound ID: 6187
Structure type: oligomer
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_135513,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_153307,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: 2768
Grossman N, Svenson SB, Leive L, Lindberg AA "Salmonella O-antigen-specific oligosaccharide-octyl conjugates activate complement via the alternative pathway at different rates depending on the structure of the O antigen" -
Molecular Immunology 27 (1990) 859-865
Artificial Salmonella serogroup B, D or Cl-specific glycolipids were prepared by covalently linking oligosaccharides corresponding to two O-antigen repeating units, obtained by phage enzyme hydrolysis of native O-antigenic polysaccharides, to octyl residues. Sheep erythrocytes coated with the artificial glycolipids were studied for their ability to consume C3, when incubated in C4- deficient guinea pig serum. Salmonella C1 (0-6,7) glycolipid-coated erythrocytes consumed C3 40% more efficiently than Salmonella D (0-9,12) glycolipid-coated erythrocytes, and 10-times more efficiently than Salmonella B (0-4,12) glycolipid-coated erythrocytes. These results resemble C3 consumption by Salmonella C1, D, and B cells and by sheep erythrocytes coated with purified lipopolysaccharides of these O-specificities. The results prove directly that in a particulate system C3 activation via the alternative pathway depends on the structural properties of the O-antigenic side chain. Structures as small as octasaccharides, or as two O-antigenic repeating units, are sufficient for triggering C3 activation, but the magnitude of activation depends on the nature of the monosaccharides. Apparently, neither the core oligosaccharide nor Lipid A of lipopolysaccharide are required for C3 activation via the alternative pathway
NCBI PubMed ID: 1699120Journal NLM ID: 7905289Publisher: Elsevier
Institutions: Laboratory of Structural Biology, National Institute of Arthritis, Diabetes, and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892
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7. Compound ID: 6451
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a-Abep2Ac-(1-3)-+ a-D-Glcp-(1-4)-+
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-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_153307,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: 1673
Whitfield C, Valvano MA "Biosynthesis and expression of cell-surface polysaccharides in gram-negative bacteria" -
Advances in Microbial Physiology 35 (1993) 135-246
This chapter provides an overview of the molecular mechanisms involved in synthesis and expression of cell-surface polysaccharides in Gram-negative bacteria. Biosynthesis of many cell-surface components, including polysaccharides, involves enzymes and enzyme complexes found in the cytoplasmic membrane. The peptidoglycan layer is located immediately external to the cytoplasmic membrane and this layer is required for cell shape and rigidity. Gram-negative bacteria possess a periplasm that contains a variety of proteins and enzymes, including some involved in import and export of macromolecules. Biosynthesis of bacterial cell-surface polysaccharides involves a series of sequential processes: (1) biosynthesis of activated precursors in the cytoplasm, (2) formation of repeating units, (3) polymerization of repeating units, and (d) export of polysaccharides to the cell surface. The assembly of polysaccharide repeating units and subsequent polymerization reactions occur at the cytoplasmic membrane, using precursors synthesized in the cytoplasm. Genes for biosynthesis of cell-surface polysaccharides are chromosomal and are arranged in clusters of one or more transcriptional units. The synthesis of lipopolysaccharide (LPS) may be subject to complex regulation, but on-off switching is not possible due to the essential structural requirement for the lipid A-core LPS molecule. Most bacteria use extracellular polysaccharides (EPSs) for protection, and many regulatory strategies are directed to modulating EPS synthesis in response to appropriate environmental cues. Application of genetic and biochemical approaches has facilitated detailed analysis of complex, multicomponent systems, such as those involved in synthesis of cell-surface polysaccharides.
NCBI PubMed ID: 8310880Publication DOI: 10.1016/S0065-2911(08)60099-5Journal NLM ID: 0117147Institutions: Department of Microbiology, University of Guelph, Ontario, Canada, Department of Microbiology, University of Guelph, Guelph, Ontario, Canada, Department of Microbiology and Immunology, University of Western Ontario, London, Ontario, Canada, N6A 5C1
- Article ID: 3846
Gajdus J, Glosnicka R, Szafranek J "Primary structure of Salmonella spp. O-antigens" -
Wiadomosci Chemiczne [Polish] 60(9-10) (2006) 621-653
Salmonella spp. are pathogenic Gram-negative bacteria that belong to Enterobacteriaceae family with lipopolysaccharide (LPS) as a constituent of cell wall. This is an integral component of the outer membrane of the wall. Salmonella smooth (S) forms produce LPS, which is composed of three parts, chemically bonded together viz. polysaccharide O-antigen, oligosaccharide core region and lipid A. Antigens O (O-PS) together with H flagella antigens are the foundation of serological classification of these bacteria. O-chain, which is built with up to 50 oligosaccharide repeating units, is one of the products of mild acidic hydrolysis of LPS. Due to the fact that polysaccharide antigens are the sites of specific antibody complexing, any difference in primary and secondary structures of O-antigens reflect serological specificity of bacteria. Taking this fact into consideration, we can distinguish about 2541 Salmonella serotypes with O and H antigenic formulas defined [4]. In this review we present 55 chemical structures of O-antigenic repeating units of Salmonella strains including their heterogeneity structures. The structures can have 22 different monosaccharide residues usually in 3 to 6 sugar repeating units. We describe here selected chemical and spectroscopic (MS, NMR) methods for primary structure examination of these bacterial O-PS. Enzymatic and immunochemical methods are also described. Cross-reactions of Salmonella spp. with any other bacteria or blood group A, B, 0 antigens are explained on the molecular level. Thus, structural assignments of somatic antigens of Salmonella spp. allow us to understand the molecular level of the classification system of these bacteria.
NMR spectroscopy, O-antigens, Salmonella, MS, primary structure
WWW link: http://baztech.icm.edu.pl/baztech/cgi-bin/btgetdoc.cgi?BUS2-0016-0014Publisher: Polish Chemical Society
Correspondence: jerzyg@chemik.chem.univ.gda.pl
Institutions: Wydzial Chemii, Uniwersytet Gdanski, ul. Sobieskiego 18, 80-952 Gdansk
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8. Compound ID: 7233
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a-Abep?Ac-(1-3)-+ a-D-Glcp-(1-4)-+
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-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
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_153307,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: 3272
Rietschel ET, Kirikae T, Schade FU, Mamat U, Schmidt G, Loppnow H, Ulmer AJ, Zähringer U, Seydel U, Di Padova F, Schreier M, Brade H "Bacterial endotoxin: Molecular relationships of structure to activity and function" -
FASEB Journal 8 (1994) 217-225
Endotoxins of Gram-negative microbes fulfill as components of the outer membrane a vital function for bacterial viability and, if set free, induce inmammalians potent pathophysiological effects. Chemically, they are lipopolysaccharides (LPS) consisting of an 0-specific chain, a core oligosaccharide, and a lipid component, termed lipid A. The latter determines the endotoxicactivities and, together with the core constituent Kdo, essential functions for bacteria. The primary structure of lipid A of various bacterial origin has been elucidated and lipid A of Escherichia coli has been chemically synthesized. The biological analysis of synthetic lipid A partial structures proved that the expression of endotoxic activity depends on a unique primary structure and a peculiar endotoxic conformation. The biological lipid A effects are mediated by macrophage-derived bioactive peptides such as tumor necrosis factor a (TNF). Macrophages possess LPS receptors, and the lipid A regions involved in specific binding and cell activation have been characterized. Synthetic lipid A partial structures compete the specific binding of LPS or lipid A and antagonistically inhibit the production of LPS-induced TNF. LPS toxicity, in general, and the ability of LPS to induce TNF are also suppressed by a recently developed monoclonal antibody (IgG2a), which is directed against an epitope located in the core oligosaccharide. At present we determine molecular and submolecular details of the specificity of the interaction of lipid A with responsive host cells with the ultimate aim to provide pharmacological or immunological therapeutics that reduce or abolish the fatal inflammatory consequences of endotoxicosis.
Lipopolysaccharide, lipid A, endotoxin, activity, function, Gram-negative, tumor necrosis factor, interleukin 1, anti-LPS antibodies, LPS antagonists - monocytes, sphingogiycoiipid
NCBI PubMed ID: 8119492Journal NLM ID: 8804484Publisher: Bethesda, MD: Federation of American Societies for Experimental Biology
Institutions: Forschungsinstitut Borstel, Institut für Experimentelle Biologie und Medizin, Germany
Methods: biological assays
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9. Compound ID: 7702
|
a-Abep2Ac-(1-3)-+
|
-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_144983,IEDB_151528,IEDB_152206,IEDB_153307,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: 3441
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: 4326
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, NMR-2D, methylation, SDS-PAGE, sugar analysis, de-O-acetylation, NMR-1D, GPC, immunoblotting
- Article ID: 4702
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, NMR-2D, methylation, GLC-MS, sugar analysis, acid hydrolysis, GLC, mild acid hydrolysis, de-O-acetylation, NMR-1D, HPLC, HPAEC-PAD, SEC
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10. Compound ID: 10394
|
a-Abep2Ac-(1-3)-+ a-D-Glcp-(1-6)-+
| |
-4)-a-D-Manp-(1-4)-b-L-Rhap-(1-3)-b-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_135513,IEDB_136044,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_153307,IEDB_190606,IEDB_225177,IEDB_433717,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: 4317
Huang JX, Azad MA, Yuriev E, Baker MA, Nation RL, Li J, Cooper MA, Velkov T "Molecular Characterization of Lipopolysaccharide Binding to Human a-1-Acid Glycoprotein" -
Journal of Lipids 2012 (2012) 475153
The ability of AGP to bind circulating lipopolysaccharide (LPS) in plasma is believed to help reduce the proinflammatory effect of bacterial lipid A molecules. Here, for the first time we have characterized human AGP binding characteristics of the LPS from a number of pathogenic Gram-negative bacteria: Escherichia coli, Salmonella typhimurium, Klebsiella pneumonia, Pseudomonas aeruginosa, and Serratia marcescens. The binding affinity and structure activity relationships (SAR) of the AGP-LPS interactions were characterized by surface plasma resonance (SPR). In order to dissect the contribution of the lipid A, core oligosaccharide and O-antigen polysaccharide components of LPS, the AGP binding affinity of LPS from smooth strains, were compared to lipid A, Kdo2-lipid A, R(a), R(d), and R(e) rough LPS mutants. The SAR analysis enabled by the binding data suggested that, in addition to the important role played by the lipid A and core components of LPS, it is predominately the unique species- and strain-specific carbohydrate structure of the O-antigen polysaccharide that largely determines the binding affinity for AGP. Together, these data are consistent with the role of AGP in the binding and transport of LPS in plasma during acute-phase inflammatory responses to invading Gram-negative bacteria.
O-antigen, lipid A, gram negative bacteria, lipopolysaccharide-binding, AGP binding, SPR
NCBI PubMed ID: 23316371Publication DOI: 10.1155/2012/475153Journal NLM ID: 101553819Publisher: Cairo: Hindawi Pub Corp
Correspondence: Tony Velkov
Institutions: Institute for Molecular Bioscience, The University of Queensland, 306 Carmody Road, St. Lucia, QLD 4072, Australia, Drug Development and Innovation, Drug Delivery, Disposition and Dynamics, Monash Institute of Pharmaceutical Sciences, Monash University, 381 Royal Parade, Parkville, VIC 3052, Australia, Medicinal Chemistry, Monash Institute of Pharmaceutical Sciences, Monash University, 381 Royal Parade, Parkville, VIC 3052, Australia, Priority Research Centre in Reproductive Science, School of Environmental and Life Sciences, University of Newcastle, Callaghan, NSW 2308, Australia
Methods: molecular modeling, fluorescence spectroscopy, surface plasmon resonance (SPR)
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11. Compound ID: 10415
|
a-Abep2(%)Ac-(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_153307,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: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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12. Compound ID: 10416
|
a-Abep2(%)Ac-(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_153307,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: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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13. Compound ID: 10449
|
a-Abep2(%)Ac-(1-3)-+
|
-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
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_153307,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: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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14. Compound ID: 10656
|
a-Abep2(%)Ac-(1-3)-+ /Variants 0/-+
| |
-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1-
/Variants 0/ is:
?%a-D-Glcp-(1-6)-
OR (exclusively)
?%a-D-Glcp-(1-4)- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: 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_153307,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: 4354
Micoli F, Rondini S, Gavini M, Pisoni I, Lanzilao L, Colucci AM, Giannelli C, Pippi F, Sollai L, Pinto V, Berti F, Maclennan CA, Martin LB, Saul A "A scalable method for O-antigen purification applied to different Salmonella serovars" -
Analytical Biochemistry 434(1) (2012) 136-145
The surface lipopolysaccharide of Gram-negative bacteria is both a virulence factor and a B-cell antigen. Antibodies against O-antigen of lipopolysaccharide may confer protection against infection, and O-antigen conjugates have been designed against multiple pathogens. Here, we describe simplified methodology for extraction and purification of O-antigen-core portion of Salmonella lipopolysaccharide, suitable for large scale production. Lipopolysaccharide extraction and delipidation is performed by acetic acid hydrolysis of whole bacterial culture, and can take place directly in a bioreactor, without previous isolation and inactivation of bacteria. Further O-antigen-core purification consists of rapid filtration and precipitation steps, without using enzymes or hazardous chemicals. The process was successfully applied to different Salmonella enterica serovars (Paratyphi A, Typhimurium and Enteritidis), obtaining good yields of high quality material, suitable for conjugate vaccines preparations.
Lipopolysaccharide, O-antigen, Salmonella
NCBI PubMed ID: 23142430Publication DOI: 10.1016/j.ab.2012.10.038Journal NLM ID: 0370535Publisher: Academic Press
Correspondence: francesca.micoli@novartis.com
Institutions: Novartis Vaccines Institute for Global Health, 53100 Siena, Italy, Novartis Vaccines and Diagnostics, 53100 Siena, Italy, MRC Centre for Immune Regulation, School of Immunity and Infection, College of Medicine and Dental Sciences, University of Birmingham, Birmingham B15 2TT, UK
Methods: 1H NMR, sugar analysis, HPLC, HPSEC, HPAEC-PAD, extraction, HR-MAS NMR, delipidation, acid hydrolyssis
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15. Compound ID: 10736
|
a-Abep2Ac-(1-3)-+
|
-2)-a-D-Manp-(1-4)-b-L-Rhap-(1-3)-b-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_135513,IEDB_136044,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_153307,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: 4368
Patel KB, Toh E, Fernandez XB, Hanuszkiewicz A, Hardy GG, Brun YV, Bernards MA, Valvano MA "Functional characterization of UDP-Glucose:Undecaprenyl-Phosphate Glucose-1-Phosphate Transferases of Escherichia coli and Caulobacter crescentus" -
Journal of Bacteriology 194(10) (2012) 2646-2657
Escherichia coli K-12 WcaJ and Caulobacter crescentus HfsE, PssY and PssZ enzymes are predicted to initiate the synthesis of colanic acid (CA) capsule and holdfast polysaccharide, respectively. These proteins belong to a prokaryotic family of membrane enzymes that catalyze the formation of a phosphoanhydride bond joining a hexose-1-phosphate with undecaprenyl phosphate (Und-P). Here, in vivo complementation assays of an E. coli K-12 wcaJ mutant demonstrate that WcaJ and PssY can complement CA synthesis. Furthermore, WcaJ can restore holdfast production in C. crescentus. In vitro transferase assays demonstrated that both WcaJ and PssY utilize UDP-glucose but not UDP-galactose. However, in a strain of Salmonella enterica Typhimurium deficient in the WbaP O antigen initiating galactosyltransferase, complementation with WcaJ or PssY resulted in O antigen production. GC-MS analysis of the LPS revealed the attachment of both CA and O antigen molecules to lipid A-core OS. Therefore, while UDP-glucose is the preferred substrate of WcaJ and PssY, these enzymes can also utilize UDP-galactose. This unexpected feature of WcaJ and PssY may help map specific residues responsible for the nucleotide diphosphate specificity in these or similar enzymes. Also, the reconstitution of O antigen synthesis in Salmonella, CA capsule in E. coli and holdfast provide biological assays of high sensitivity to examine the sugar-1-phosphate transferase specificity of heterologous proteins.
O-antigen, specificity, Salmonella enterica, galactosyltransferase, colanic acid, Typhimurium, UDP-glucose, Escherichia coli K12, Caulobacter crescentus
NCBI PubMed ID: 22408159Publication DOI: 10.1128/JB.06052-11Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: Miguel A. Valvano
Institutions: Departments of Microbiology and Immunology, University of Western Ontario, London, Ontario, Canada
Methods: DNA sequencing, GC-MS, SDS-PAGE, glycosyltransferase assays, genetic methods
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