Found 22 structures.
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1. Compound ID: 996
a-Parp-(1-3)-+ a-D-Glcp-(1-6)-+
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-2)-a-D-Manp-(1-4)-a-L-Rhap3Ac-(1-3)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_136035,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174034,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: 295
Konadu EY, Lin FYC, Ho VA, Thuy NTT, Bay PV, Thanh TC, Khiem HB, Trach DD, Karpas AB, Li J, Bryla DA, Robbins JB, Szu SC "Phase 1 and phase 2 studies of Salmonella enterica serovar Paratyphi A O-specific polysaccharide-tetanus toxoid conjugates in adults, teenagers, and 2-to 4-year-old children in Vietnam" -
Infection and Immunity 68(3) (2000) 1529-1534
Salmonella enterica serovar Paratyphi A O-specific polysaccharide (O-SP) was activated with 1-cyano-4-dimethylaminopyridinium tetrafluoroborate (CDAP) and bound to tetanus toxoid (TT) with adipyl dihydrazide as a linker (SPA-TT(1)) or directly (SPA-TT(2)). In mice, these two conjugates elicited high levels of immunoglobulin G (IgG) anti-lipopolysaccharide (LPS) in serum with bactericidal activity (E. Konadu, J. Shiloach, D. A. Bryla, J. B. Robbins, and S. C. Szu, Infect. Immun. 64:2709-2715, 1996). The safety and immunogenicity of the two conjugates were then evaluated sequentially in Vietnamese adults, teenagers, and 2- to 4-year-old children. None of the vaccinees experienced significant side effects, and all had preexisting LPS antibodies. At 4 weeks after injection, there were significant increases of the geometric mean IgG and IgM anti-LPS levels in the adults and teenagers: both conjugates elicited a greater than fourfold rise in the IgG anti-LPS level in serum in >/=80% of the volunteers. SPA-TT(2) elicited slightly higher, though not statistically significantly, levels of IgG anti-LPS than did SPA-TT(1) in these age groups. Accordingly, only SPA-TT(2) was evaluated in the 2- to 4-year-old children. On a random basis, one or two injections were administered 6 weeks apart to the children. No significant side effects were observed, and the levels of preexisting anti-LPS in serum were similar in children of all ages. A significant rise in the IgG anti-LPS titer was elicited by the first injection (P = 0.0001); a second injection did not elicit a booster response. Representative sera from all groups had bactericidal activity that could be adsorbed by S. enterica serovar Paratyphi A LPS.
phase, O-specific, Salmonella, Salmonella enterica, Adult, conjugate, conjugates, children
NCBI PubMed ID: 10678970Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: scszu@helix.nih.gov
Institutions: National Institute of Child Health and Human Development, National Institutes of Health, Bethesda, MD, USA, Huu Nghi Hospital, Cao La?nh District, Dong Thap Province, Pasteur Institut, Ho Chi Minh City, and National Institute of Hygiene and Epidemiology, Hanoi, Vietnam.
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2. Compound ID: 2586
a-Parp-(1-3)-+ a-D-Glcp-(1-6)-+
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-2)-a-D-Man-(1-4)-a-L-Rhap3Ac-(1-3)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_136035,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174034,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: 887
Konadu E, Shiloach J, Bryla DA, Robbins JB, Szu SC "Synthesis, characterization, and immunological properties in mice of conjugates composed of detoxified lipopolysaccharide of Salmonella paratyphi A bound to tetanus toxoid, with emphasis on the role of O acetyls" -
Infection and Immunity 64 (1996) 2709-2715
Lipopolysaccharide, synthesis, antigen, LPS, role, characterization, property, immunological, mice, Salmonella, bound, conjugate, conjugates, tetanus toxoid, acetyl, O-acetyl, detoxified, Salmonella paratyphi, tetanus, toxoid
Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: National Institute of Health, Bethesda, Maryland, USA, NationalInstitute of Health, Bethesda, Maryland, USA
Methods: NMR
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3. Compound ID: 2587
a-Parp-(1-3)-+ a-D-Glcp-(1-6)-+
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-2)-a-D-Man-(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
Contained glycoepitopes: IEDB_130701,IEDB_136035,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174034,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: 887
Konadu E, Shiloach J, Bryla DA, Robbins JB, Szu SC "Synthesis, characterization, and immunological properties in mice of conjugates composed of detoxified lipopolysaccharide of Salmonella paratyphi A bound to tetanus toxoid, with emphasis on the role of O acetyls" -
Infection and Immunity 64 (1996) 2709-2715
Lipopolysaccharide, synthesis, antigen, LPS, role, characterization, property, immunological, mice, Salmonella, bound, conjugate, conjugates, tetanus toxoid, acetyl, O-acetyl, detoxified, Salmonella paratyphi, tetanus, toxoid
Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: National Institute of Health, Bethesda, Maryland, USA, NationalInstitute of Health, Bethesda, Maryland, USA
Methods: NMR
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4. Compound ID: 3379
a-Parp-(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- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_136035,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174034,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: 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: 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: 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: 3651
a-Parp-(1-3)-+
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-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_136035,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_174034,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: 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: 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: 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: 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
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6. Compound ID: 5090
a-Parp-(1-3)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1--/(->1) 4-nitrophenol/ |
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Structure type: oligomer
Aglycon: (->1) 4-nitrophenol
Contained glycoepitopes: IEDB_130701,IEDB_136035,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_174034,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: 2029
Bock K, Meldal M, Bundle DR, Iversen T, Pinto BM, Garegg PJ, Kvanström I, Norberg T, Lindberg AA, Svenson SB "The conformation of Salmonella O-antigenic oligosaccharides of serogroups A, B, and D1 inferred from 1H- and 13C-nuclear magnetic resonance spectroscopy" -
Carbohydrate Research 130 (1984) 35-53
The conformational model derived by the HSEA calculation method was used to interpret the n.m.r. data for solutions of oligosaccharides corresponding to the Salmonella serogroups A, B, and D1 antigenic determinants. The favored conformer, derived by calculation, accounted for the observed, chemical-shift changes and accurately predicted the existence and magnitude of inter-ring proton n.O.e.'s. Extensive proton-density and compression of proton, Van der Waals radii were correlated with deshielding of specific proton-resonances. The model of lipopolysaccharide conformation accounts for the known antigenic properties of Salmonella O-antigens.
NCBI PubMed ID: 6478461Publication DOI: 10.1016/0008-6215(84)85268-4Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, Stockholm, Sweden, Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario K1A OR6 Canada, Department of Bacteriology, National Bacteriological Laboratory, S-105 21 Stockholm, Sweden, Department of Organic Chemistry, The Technical University of Denmark, 2800 Lyngby Denmark
Methods: 13C NMR, 1H NMR, conformation analysis, nOe, HSEA
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7. Compound ID: 6088
a-Parp-(1-3)-+ a-Parp-(1-3)-+
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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 |
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Structure type: oligomer
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_136035,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141798,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_174034,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
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8. Compound ID: 6089
a-Parp-(1-3)-+ a-Parp-(1-3)-+ a-Parp-(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 |
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Structure type: oligomer
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_136035,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141798,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_174034,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
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9. Compound ID: 6452
a-Par-(1-3)-+ a-D-Glcp-(1-4)-+
| |
-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_130701,IEDB_136035,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174034,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
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10. Compound ID: 6453
a-Par-(1-3)-+ a-D-Glcp-(1-6)-+
| |
-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_130701,IEDB_136035,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174034,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
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11. Compound ID: 7695
a-Parp-(1-3)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1--/p-aminophenyl/ |
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Structure type: oligomer
Aglycon: p-aminophenyl
Trivial name: tetrasaccharide conjugate
Contained glycoepitopes: IEDB_130701,IEDB_136035,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_174034,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
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12. Compound ID: 8358
a-Parp-(1-3)-+ ?%D-Glcp-(1-4)-+
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-2)-a-D-Manp-(1-4)-a-L-Rhap3(%)Ac-(1-3)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_136035,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174034,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: 3635
Hellerqvist CG, Lindberg B, Samuelsson K, Lindberg AA "Structural studies on the O-specific side-chains of the cell-wall lipopolysaccharide from Salmonella paratyphi A var. durazzo" -
Acta Chemica Scandinavica 25 (1971) 955-961
The structure of the O-specific side-chains of the cell-wall lipopolysaccharide (LPS) of S. paratyphi A var. durazzo has been investigated. Methylation analyses of the original LPS, of the material obtained on mild hydrolysis of the LPS with acid, and of a product obtained by acetalation of the free hydroxyl groups in the LPS, have provided the essential information in the study. The mixtures of sugars obtained were analysed, as alditol acetates, by GLC-mass spectrometrey. A trisaccharide isolated after acid hydrolysis of the LPS was isolated and identified. As a result of these studies, a detailed structure of the repeating unit of these side-chain is presented.
Lipopolysaccharide, structural, side chain, O-specific, cell wall, Salmonella, structural studies, Salmonella paratyphi, Salmonella paratyphi A
NCBI PubMed ID: 5117491Journal NLM ID: 0421263Publisher: Munksgaard International Publishers
Institutions: Institutionen for organisk kemi, Stockholms universitet, S-113 27 Stockholm, and Statens bakteriologiska laboratorium, Stockholm, Sweden
Methods: methylation, IR, GLC, mild acid hydrolysis, MS
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13. Compound ID: 10414
a-Parp-(1-3)-+ a-D-Glcp-(1-4)-+
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-2)-a-D-Manp-(1-4)-a-L-Rhap2(%)Ac-(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_130422,IEDB_130701,IEDB_136035,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174034,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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14. Compound ID: 10654
a-Parp-(1-3)-+ ?%a-D-Glcp-(1-6)-+
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-2)-a-D-Manp-(1-4)-a-L-Rhap3(%)Ac-(1-3)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_136035,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174034,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: 11422
a-Parp-(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_130701,IEDB_136035,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_174034,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
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