Found 16 structures.
Displayed structures from 1 to 15
Next 15 structure(s)
Expand all compounds
Collapse all compounds
Show all as text (SweetDB notation)
Show all graphically (SNFG notation)
1. Compound ID: 263
|
a-Tyvp-(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, CPS
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_174035,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: 68
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: 1368
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: 1407
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: 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: 3243
Snyder DS, Gibson D, Heiss C, Kay W, Azadi P "Structure of a capsular polysaccharide isolated from Salmonella enteritidis" -
Carbohydrate Research 341(14) (2006) 2388-2397
Salmonella enteritidis is a food-borne enteric human pathogen that can form a complex protective extracellular matrix. We describe here a component of this matrix which is distinct from other known salmonella extracellular polysaccharides such as cellulose and colanic acid. We have used glycosyl composition and linkage analysis, as well as 1D and 2D NMR spectroscopy to determine the structure of this polysaccharide. We propose that the primary saccharide in the S. enteritidis capsule has a branched tetrasaccharide repeating unit having the following structure: →3)-α-D-Galp-(1→2)-[α-Tyvp-(1→3)]-α-D-Manp-(1→4)-α-L-Rhap-(1→. This structure is partially substituted on both tyvelose and galactose with a glucose-containing side chain. It further bears considerable similarity to the O antigen from this organism, a feature found in a number of other capsules from Gram-negative bacteria. In addition, we have detected fatty acids at levels that indicate the presence of a lipid anchor.
Extracellular matrix; Capsule; Salmonella; O Antigen; Capsular polysaccharide; Glycolipid
Publication DOI: 10.1016/j.carres.2006.06.010Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: azadi@ccrc.uga.edu
Institutions: Complex Carbohydrate Research Center, Athens, GA 30602-4712, USA, Department of Biochemistry and Microbiology, University of Victoria, Victoria, BC, Canada V8W 3P6
Methods: NMR, composition analysis, linkage analysis
- Article ID: 3284
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, capsular polysaccharide, epitope, monoclonal antibodies, 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: 3601
Son S, Tano C, Furuike T, Sakairi N "Synthesis of a tetrasaccharide repeating unit of O-antigenic polysaccharide of Salmonella enteritidis by use of unique and odorless dodecyl thioglycosyl donors" -
Tetrahedron Letters 49(36) (2008) 5289-5292
The first total synthesis of a unique tetrasaccharide repeating unit of lipopolysaccharide from Salmonella enteritidis has been accomplished by assembly of dodecyl thioglycosides. The crucial key steps were preparation of a rare branched dideoxy sugar, dtyvelose (3,6-dideoxy-d-arabino-d-hexose) and sequential regioselective glycosylation at 2,3-positions of a central d-mannose residue 5 with d-tyvelose 6 and d-galactose donors 7.
synthesis, tetrasaccharide, O-antigenic polysaccharide, glycosylation, Salmonella enteritidis
Publication DOI: 10.1016/j.tetlet.2008.06.097Journal NLM ID: 2984819RPublisher: Elsevier
Correspondence: nsaka@ees.hokudai.ac.jp (N. Sakairi)
Institutions: Graduate School of Environmental Science, Hokkaido University, Kita-ku, Sapporo 060-0810, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, chemical synthesis, glycosylation
- Article ID: 3746
Olsson JD, Landstrom J, Ronnols J, Oscarson S, Widmalm G "Synthesis of and molecular dynamics simulations on a tetrasaccharide corresponding to the repeating unit of the capsular polysaccharide from Salmonella enteritidis" -
Organic and Biomolecular Chemistry 7(8) (2009) 1612-1618
Syntheses of two oligosaccharides as methyl glycosides related to the repeating unit of S. enteritidis capsular polysaccharide (CPS) are presented. The trisaccharide corresponds to the backbone of the CPS whereas the tetrasaccharide is a model for the repeating unit which has a branched structure. Molecular dynamics simulations investigating their flexibility and dynamics revealed that the oligosaccharides populate several conformational states and indicate that conformational averaging should be used in describing the accessible conformational space.
synthesis, capsular polysaccharide, conformational, molecular dynamics, Salmonella enteritidis
NCBI PubMed ID: 19343247Publication DOI: 10.1039/b823428kJournal NLM ID: 101154995Publisher: The Royal Society of Chemistry
Correspondence: G. Widmalm
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
Methods: 13C NMR, 1H NMR, chemical methods, MD simulations
- 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
- Article ID: 4314
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: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 4476
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: 4682
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: 6102
Liu MA, Kidambi A, Reeves PR "The low level of O antigen in Salmonella enterica Paratyphi A is due to inefficiency of the glycosyltransferase WbaV" -
FEMS Microbiology Letters 368(3) (2021) fnab009
The group A O antigen is the major surface polysaccharide of Salmonella enterica serovar Paratyphi A (SPA), and the focal point for most current vaccine development efforts. The SPA O-antigen repeat (O unit) is structurally similar to the group D1 O unit of S. enterica serovar Typhi, differing only in the presence of a terminal side-branch paratose (Par) in place of tyvelose (Tyv), both of which are attached by the glycosyltransferase WbaV. The two O-antigen gene clusters are also highly similar, but with a loss-of-function mutation in the group A tyv gene and the tandem amplification of wbaV in most SPA strains. In this study, we show that SPA strains consistently produce less O antigen than their group D1 counterparts and use an artificial group A strain (D1 Deltatyv) to show this is due to inefficient Par attachment by WbaV. We also demonstrate that group A O-antigen production can be increased by overexpression of the wbaV gene in both the D1 Deltatyv strain and two multi-wbaV SPA strains. These findings should be broadly applicable in ongoing vaccine development pipelines, where efficient isolation and purification of large quantities of O antigen is of critical importance
biosynthesis, O antigen, glycosyltransferase, paratose, Paratyphi A, WbaV
NCBI PubMed ID: 33476372Publication DOI: 10.1093/femsle/fnab009Journal NLM ID: 7705721Publisher: Blackwell Publishing
Correspondence: peter.reeves@sydney.edu.au
Institutions: School of Life and Environmental Sciences, The University of Sydney, NSW 2006, Australia
Methods: PCR, SDS-PAGE, genetic methods, extraction, growth assays
Expand this compound
Collapse this compound
2. Compound ID: 3409
|
a-Tyvp-(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_130660,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136791,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_174035,IEDB_190606,IEDB_225177,IEDB_840979,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: 1259
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: 1322
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: 1368
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: 1484
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: 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
- Article ID: 4758
Hong Y, Morcilla VA, Liu MA, Russell EL, Reeves PR "Three Wzy polymerases are specific for particular forms of an internal linkage in otherwise identical O units" -
Microbiology 163 (2015) 1639-1647
The Wzx/Wzy-dependent pathway is the predominant pathway for O-antigen production in Gram-negative bacteria. The O-antigen repeat unit (O unit) is an oligosaccharide that is assembled at the cytoplasmic face of the membrane on undecaprenyl pyrophosphate. Wzx then flips it to the periplasmic face for polymerisation by Wzy, which adds a O unit to the reducing end of a growing O-unit polymer in each round of polymerisation. Wzx and Wzy both exhibit enormous sequence diversity. We have recently determined that, contrary to earlier reports, the efficiency of diverse Wzx forms can be significantly reduced by minor structural variations to their native O-unit substrate. However, details of Wzy substrate specificity remain unexplored. The closely related galactose-initiated Salmonella O antigens present a rare opportunity to address these matters. The D1 and D2 O units differ only in an internal mannose-rhamnose linkage, and D3 expresses both in the same chain. We showed that D1 and D2 polymerases are specific for O units with their respective alpha or beta configuration for the internal mannose-rhamnose linkage. The Wzy encoded by D3 gene cluster polymerises only D1 O units, and deleting the gene does not eliminate polymeric O antigen, both observations indicating the presence of an additional wzy gene. The levels of Wzx and Wzy substrate specificity will affect the ease with which new O units can evolve, and also our ability to modify O antigens, capsules or secreted polysaccharides by glyco-engineering, to generate novel polysaccharides, as the Wzx/Wzy-dependent pathway is responsible for much of the diversity.
O-antigen, gene cluster, Salmonella, Substrate Specificity, Wzy polymerases
NCBI PubMed ID: 25987464Publication DOI: 10.1099/mic.0.000113Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: peter.reeves@sydney.edu.au
Institutions: Department of Microbiology, University of Illinois, Urbana, IL 61801, USA, University of Illinois at Urbana-Champaign, School of Molecular Bioscience, Building D17, University of Sydney, NSW 2006, Australia
Methods: PCR, SDS-PAGE, DNA techniques, genetic methods
Expand this compound
Collapse this compound
3. Compound ID: 3574
|
a-Tyvp-(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_130660,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_174035,IEDB_190606,IEDB_225177,IEDB_840979,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: 1322
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: 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
Expand this compound
Collapse this compound
4. Compound ID: 4683
|
a-Tyvp-(1-3)-+ a-D-Glcp2Ac-(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_130660,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136791,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_174035,IEDB_190606,IEDB_225177,IEDB_840979,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: 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
Expand this compound
Collapse this compound
5. Compound ID: 5743
|
a-Tyvp-(1-3)-+ a-Tyvp-(1-3)-+ a-Tyvp-(1-3)-+
| | |
a-D-Galp-(1-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-2)-a-D-Galp-(1-2)-a-D-Manp-(1-4)-a-L-Rhap |
Show graphically |
Structure type: oligomer
Compound class: LPS
Contained glycoepitopes: IEDB_130660,IEDB_130669,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_174033,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: 2504
Chernyak AY, Weintraub A, Norberg T, Kallin E "Preparation of oligosaccharide-polyacrylamide conjugates and their use as antigens in enzyme immunoassay (EIA)" -
Glycoconjugate Journal 7(2) (1990) 111-119
Oligosaccharides derived from Salmonella lipopolysaccharides or from human milk were converted to their N-acetyl-N-(4-acrylamidophenyl)-1-amino-1-deoxyalditol derivatives. These derivatives were copolymerized with acrylamide to give linear, water-soluble polymers, which were used as coating antigens in EIA assays.
Lipopolysaccharide, oligosaccharide, Salmonella, conjugate, EIA
Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, Russia, USSR, Department of Clinical Bacteriology, Karolinska Institute, Huddinge University Hospital, Huddinge, Sweden, Organic Synthesis Department, BioCarb AB, Lund, Sweden
Expand this compound
Collapse this compound
6. Compound ID: 6086
|
a-Tyvp-(1-3)-+ a-Tyvp-(1-3)-+
| |
a-D-Galp-(1-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1-2)-a-D-Manp-(1-4)-L-Rha |
Show graphically |
Structure type: oligomer
Trivial name: octasaccharide
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_141798,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_174033,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: 2711
Jörbeck HJA, Svenson SB, Lindberg AA "Immunochemistry of Salmonella O-antigens: specificity of rabbit antibodies against the O-antigen 4 determinant elicited by whole bacteria and O-antigen 4 specific saccharide-protein conjugates" -
Journal of Immunology 123(3) (1979) 1376-1381
NCBI PubMed ID: 89168Journal NLM ID: 2985117RPublisher: Bethesda, MD: American Association of Immunologists
- Article ID: 3500
Landstrom J, Nordmark EL, Eklund R, Weintraub A, Seckler R, Widmalm G "Interaction of a Salmonella enteritidis O-antigen octasaccharide with the phage P22 tailspike protein by NMR spectroscopy and docking studies" -
Glycoconjugate Journal 25(2) (2008) 137-143
The tailspike protein P22 recognizes an octasaccharide derived from the O-antigen polysaccharide of Salmonella enteritidis in a shallow groove and molecular docking successfully identifies this binding region on the protein surface. Analysis by 2D (1)H,(1)H-T-ROESY and transferred NOESY NMR experiments indicate that the bound octasaccharide ligand has a conformation similar to that observed in solution. The results from a saturation transfer difference NMR experiment show that a large number of protons in the octasaccharide are in close contact with the protein as a result of binding. A comparison of the crystal structure of the complex and a molecular dynamics simulation of the octasaccharide with explicit water molecules suggest that only minor conformational changes are needed upon binding to the tailspike protein
conformation, carbohydrates, molecular dynamics, hydrolase, docking, STD
NCBI PubMed ID: 17703358Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Correspondence: gw@organ.su.se
Institutions: Arrhenius Laboratory, Department of Organic Chemistry, Stockholm University, Stockholm, Sweden
Methods: 13C NMR, 1H NMR, NMR-2D
Expand this compound
Collapse this compound
7. Compound ID: 6087
|
a-Tyvp-(1-3)-+ a-Tyvp-(1-3)-+ a-Tyvp-(1-3)-+
| | |
a-D-Galp-(1-2)-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-(1-2)-a-D-Manp-(1-4)-L-Rha |
Show graphically |
Structure type: oligomer
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_141798,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_174035,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: 2711
Jörbeck HJA, Svenson SB, Lindberg AA "Immunochemistry of Salmonella O-antigens: specificity of rabbit antibodies against the O-antigen 4 determinant elicited by whole bacteria and O-antigen 4 specific saccharide-protein conjugates" -
Journal of Immunology 123(3) (1979) 1376-1381
NCBI PubMed ID: 89168Journal NLM ID: 2985117RPublisher: Bethesda, MD: American Association of Immunologists
Expand this compound
Collapse this compound
8. Compound ID: 6269
|
a-Tyvp-(1-3)-+ a-D-Glcp2Ac-(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
Aglycon: tetanus toxoid
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136791,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_174035,IEDB_190606,IEDB_225177,IEDB_840979,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: 2829
Saxena M, Di Fabio JL "Salmonella typhi O-polysaccharide-tetanus toxoid conjugated vaccine" -
Vaccine 12 (1994) 879-884
Journal NLM ID: 8406899Publisher: Elsevier
Expand this compound
Collapse this compound
9. Compound ID: 6445
|
a-Tyvp-(1-3)-+ Ac-2)-/Variants 0/-+
| |
-2)-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
; n=30
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136791,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_139420,IEDB_139421,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_174035,IEDB_190606,IEDB_225177,IEDB_840979,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: 2892
Hellerqvist CG, Lindberg B, Svensson S, Holme T, Lindberg AA "Structural studies on the O-specific side-chains of the cell-wall lipopolysaccharide from Salmonella typhi and S. enteritidis" -
Acta Chemica Scandinavica 23 (1969) 1588-1596
NCBI PubMed ID: 5360616Publication DOI: 10.3891/acta.chem.scand.23-1588Journal NLM ID: 0421263Publisher: Munksgaard International Publishers
Institutions: Institutionen för organisk kemi, Stockholm Universitet, Stockholm, Sweden, Bakteriologiska Institutionen, Karolinska Institutet, Stockholm, Sweden, Stateus bakteriologiska laboratorium, Stockholm, Sweden
Methods: NMR, GLC, MS, methylation analysis
Expand this compound
Collapse this compound
10. Compound ID: 7100
|
?%a-D-Glcp-(1-4)-a-Tyvp-(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: CPS
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136791,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_174035,IEDB_190606,IEDB_225177,IEDB_840979,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: 3225
Gibson DL, White AP, Snyder SD, Martin S, Heiss C, Azadi P, Surette M, Kay WW "Salmonella Produces an O-Antigen Capsule Regulated by AgfD and Important for Environmental Persistence" -
Journal of Bacteriology 188(22) (2006) 7722-7730
In this study, we show that Salmonella produces an O-antigen capsule coregulated with the fimbria- and cellulose-associated extracellular matrix. Structural analysis of purified Salmonella extracellular polysaccharides yielded predominantly a repeating oligosaccharide unit similar to that of Salmonella enterica serovar Enteritidis lipopolysaccharide O antigen with some modifications. Putative carbohydrate transport and regulatory operons important for capsule assembly and translocation, designated yihU-yshA and yihVW, were identified by screening a random transposon library with immune serum generated to the capsule. The absence of capsule was confirmed by generating various isogenic ∆yih mutants, where yihQ and yihO were shown to be important in capsule assembly and translocation. Luciferase-based expression studies showed that AgfD regulates the yih operons in coordination with extracellular matrix genes coding for thin aggregative fimbriae and cellulose. Although the capsule did not appear to be important for multicellular behavior, we demonstrate that it was important for survival during desiccation stress. Since the yih genes are conserved in salmonellae and the O-antigen capsule was important for environmental persistence, the formation of this surface structure may represent a conserved survival strategy.
gene, O-antigen, extracellular polysaccharide, transposon, Salmonella enterica, capsule, transport, cellulose, regulatory operon
NCBI PubMed ID: 17079680Publication DOI: 10.1128/JB.00809-06Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: wkay@uvic.ca
Institutions: Department of Biochemistry and Microbiology, University of Victoria, Victoria, V8W 3P6 British Columbia, Canada, Department of Microbiology and Infectious Diseases, University of Calgary, Calgary, T2N 4N1 Alberta, Canada, Complex Carbohydrate Research Center, Athens, GA, USA-47123
Methods: serological methods
Expand this compound
Collapse this compound
11. Compound ID: 7699
|
a-Tyvp-(1-3)-+ a-Tyvp-(1-3)-+ a-Tyvp-(1-3)-+
| | |
a-D-Galp-(1-2)-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-(1-2)-a-D-Manp-(1-4)-a-L-Rhap-(1--/2-aminoethyl-(N-methyl)-hydroxylamine/ |
Show graphically |
Structure type: oligomer
Aglycon: 2-aminoethyl-(N-methyl)-hydroxylamine
Trivial name: dodecasaccharide conjugate
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_174035,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: 3440
Blixt O, Hoffmann J, Svenson S, Norberg T "Pathogen specific carbohydrate antigen microarrays: a chip for detection of Salmonella O-antigen specific antibodies" -
Glycoconjugate Journal 25(1) (2008) 27-36
A Salmonella O-antigen microarray was developed by covalent coupling of oligosaccharide antigens specific for serogroups Salmonella enterica sv. Paratyphi (group A), Typhimurium (group B) and Enteritidis (group D). Antibodies were correctly detected in sera from patients with culture verified salmonellosis. High serogroup-specificity was seen with the disaccharide antigens. With the larger antigens, containing the backbone sequence Manα1-2Rhaα1-2Gal (MRG), common backbone-specific antibodies (O-antigen 12) were also detected. This is 'proof of principle' that pathogen-specific carbohydrate antigen microarrays constitute a novel technology for rapid and specific serological diagnosis in either individual patients or larger sero-epidemiological and vaccine studies.
oligosaccharide, polysaccharide, antibody, vaccine, salmonellosis, glycanarray
NCBI PubMed ID: 17558551Publication DOI: 10.1007/s10719-007-9045-0Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Correspondence: olablixt@scripps.edu
Institutions: Department of Molecular Biology, Glycan Array Synthesis Core D, Consortium for Functional Glycomics. The Scripps Research Institute, CB 248A 10550 N. Torrey Pines Road, La Jolla, CA, 92037, USA
Methods: serological methods
Expand this compound
Collapse this compound
12. Compound ID: 10420
|
a-Tyvp-(1-3)-+ ?%a-D-Glcp2Ac-(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_130660,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136791,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_174035,IEDB_190606,IEDB_225177,IEDB_840979,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: 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
Expand this compound
Collapse this compound
13. Compound ID: 11423
|
a-Tyvp-(1-3)-+
|
-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer biological repeating unit
Aglycon: ->P-P) undecaprenol pyrophosphate
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_174035,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: 4607
Reeves PR, Cunneen MM, Liu B, Wang L "Genetics and evolution of the Salmonella galactose-initiated set of O antigens" -
PLoS One 8(7) (2013) e69306
This paper covers eight Salmonella serogroups, that are defined by O antigens with related structures and gene clusters. They include the serovars that are now most frequently isolated. Serogroups A, B1, B2, C2-C3, D1, D2, D3 and E have O antigens that are distinguished by having galactose as first sugar, and not N-acetyl glucosamine or N-acetyl galactosamine as in the other 38 serogroups, and indeed in most Enterobacteriaceae. The gene clusters for these galactose-initiated appear to have entered S. enterica since its divergence from E. coli, but sequence comparisons show that much of the diversification occurred long before this. We conclude that the gene clusters must have entered S. enterica in a series of parallel events. The individual gene clusters are discussed, followed by analysis of the divergence for those genes shared by two or more gene clusters, and a putative phylogenic tree for the gene clusters is presented. This set of O antigens provides a rare case where it is possible to examine in detail the relationships of a significant number of O antigens. In contrast the more common pattern of O-antigen diversity within a species is for there to be only a few cases of strains having related gene clusters, suggesting that diversity arose through gain of individual O-antigen gene clusters by lateral gene transfer, and under these circumstances the evolution of the diversity is not accessible. This paper on the galactose-initiated set of gene clusters gives new insights into the origins of O-antigen diversity generally.
genetics, gene cluster, O-antigens, Salmonella, evolution
NCBI PubMed ID: 23874940Publication DOI: 10.1371/journal.pone.0069306Journal NLM ID: 101285081Publisher: San Francisco, CA: Public Library of Science
Correspondence: peter.reeves@sydney.edu.au
Institutions: School of Molecular Bioscience, University of Sydney, Sydney, Australia, TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, P. R. China
Methods: DNA techniques, genetic methods
Expand this compound
Collapse this compound
14. Compound ID: 11713
|
a-Tyvp-(1-3)-+ a-D-Glcp2Ac-(1-4)-+
| |
-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136791,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_174035,IEDB_190606,IEDB_225177,IEDB_840979,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: 4696
Liu B, Knirel YA, Feng L, Perepelov AV, Senchenkova SN, Reeves P, Wang L "Structural diversity in Salmonella O antigens and its genetic basis" -
FEMS Microbiology Reviews 38(1) (2014) 56-89
This review covers the structures and genetics of the 46 O antigens of Salmonella, a major pathogen of humans and domestic animals. The variation in structures underpins the serological specificity of the 46 recognized serogroups. The O antigen is important for the full function and virulence of many bacteria, and the considerable diversity of O antigens can confer selective advantage. Salmonella O antigens can be divided into two major groups: those which have N-acetylglucosamine (GlcNAc) or N-acetylgalactosamine (GalNAc) and those which have galactose (Gal) as the first sugar in the O unit. In recent years, we have determined 21 chemical structures and sequenced 28 gene clusters for GlcNAc-/GalNAc-initiated O antigens, thus completing the structure and DNA sequence data for the 46 Salmonella O antigens. The structures and gene clusters of the GlcNAc-/GalNAc-initiated O antigens were found to be highly diverse, and 24 of them were found to be identical or closely related to Escherichia coli O antigens. Sequence comparisons indicate that all or most of the shared gene clusters were probably present in the common ancestor, although alternative explanations are also possible. In contrast, the better-known eight Gal-initiated O antigens are closely related both in structures and gene cluster sequences.
polysaccharide, glycosyltransferase, pathogen, serotyping, evolution, polymorphism
NCBI PubMed ID: 23848592Publication DOI: 10.1111/1574-6976.12034Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: wanglei@nankai.edu.cn
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, Tianjin Key Laboratory of Microbial Functional Genomics, Tianjin, China, Tianjin Research Center for Functional Genomics and Biochip, Tianjin, China, The Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, Tianjin, China, School of Molecular and Microbial Bioscience (G08), University of Sydney, Sydney, Australia
Expand this compound
Collapse this compound
15. Compound ID: 11714
|
a-Tyvp-(1-3)-+
|
-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_174035,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: 4696
Liu B, Knirel YA, Feng L, Perepelov AV, Senchenkova SN, Reeves P, Wang L "Structural diversity in Salmonella O antigens and its genetic basis" -
FEMS Microbiology Reviews 38(1) (2014) 56-89
This review covers the structures and genetics of the 46 O antigens of Salmonella, a major pathogen of humans and domestic animals. The variation in structures underpins the serological specificity of the 46 recognized serogroups. The O antigen is important for the full function and virulence of many bacteria, and the considerable diversity of O antigens can confer selective advantage. Salmonella O antigens can be divided into two major groups: those which have N-acetylglucosamine (GlcNAc) or N-acetylgalactosamine (GalNAc) and those which have galactose (Gal) as the first sugar in the O unit. In recent years, we have determined 21 chemical structures and sequenced 28 gene clusters for GlcNAc-/GalNAc-initiated O antigens, thus completing the structure and DNA sequence data for the 46 Salmonella O antigens. The structures and gene clusters of the GlcNAc-/GalNAc-initiated O antigens were found to be highly diverse, and 24 of them were found to be identical or closely related to Escherichia coli O antigens. Sequence comparisons indicate that all or most of the shared gene clusters were probably present in the common ancestor, although alternative explanations are also possible. In contrast, the better-known eight Gal-initiated O antigens are closely related both in structures and gene cluster sequences.
polysaccharide, glycosyltransferase, pathogen, serotyping, evolution, polymorphism
NCBI PubMed ID: 23848592Publication DOI: 10.1111/1574-6976.12034Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: wanglei@nankai.edu.cn
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, Tianjin Key Laboratory of Microbial Functional Genomics, Tianjin, China, Tianjin Research Center for Functional Genomics and Biochip, Tianjin, China, The Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, Tianjin, China, School of Molecular and Microbial Bioscience (G08), University of Sydney, Sydney, Australia
Expand this compound
Collapse this compound
Next 15 structure(s)
Total list of structure IDs on all result pages of the current query:
Total list of corresponding CSDB IDs (record IDs):
Execution: 9 sec