Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136105,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_139420,IEDB_139421,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_7,SB_72

• Article ID: 50
  Dziadziuszko H, Kunikowska D, Glosnicka R, Gajdus J, Kaczyński Z, Szafranek J "Immunological and chemical studies of Salmonella haarlem somatic antigen epitopes. II. Serological investigations" - FEMS Immunology and Medical Microbiology 21(4) (1998) 253-259
  

  Lipopolysaccharide (LPS) of Salmonella haarlem was hydrolyzed and the products separated. The structure of the O-specific polysaccharide (OPS) was found from sugar and methylation analyses. Rhamnose, mannose, galactose and tyvelose were detected and their linkage modes were established. The structure was confirmed by 1H, homonuclear and heteronuclear correlations and 13C NMR spectra. Anomeric configurations were assigned by chromium trioxide oxidation and proton coupled 13C spectra. Sugar sequence was established from specific carbon shift data and nuclear Overhauser effect spectroscopy. The repeating unit structure of S. haarlem OPS as →3)-α-D-Galp-(1→6)-[α-Tyvp-(1→3)]-β-D-Manp-(1→4)-α-L-Rhap was estimated. No structural heterogeneity of the antigen was found

  Lipopolysaccharide, structure, monoclonal antibody, O-polysaccharide, Salmonella, Rabbit antiserum

  NCBI PubMed ID: 9752996
  Journal NLM ID: 9315554
  Publisher: Elsevier
  Correspondence: janat@chemik.chem.univ.gda.pl
  Institutions: Department of Chemistry, University of Gdansk, Poland
  Methods: Smith degradation
  
   
  
  Salmonella haarlem
  CSDB ID 2027 (all data & tools)
• Article ID: 1408
  Curd H, Liu D, Reeves PR "Relationships among the O-antigen gene clusters of Salmonella enterica groups B, D1, D2, and D3" - Journal of Bacteriology 180(4) (1998) 1002-1007
  

  The O antigen is an important cell wall antigen of gram-negative bacteria, and the genes responsible for its biosynthesis are located in a gene cluster. We have cloned and sequenced the DNA segment unique to the O-antigen gene cluster of Salmonella enterica group D3. This segment includes a novel O-antigen polymerase gene (wzyD3). The polymerase gives α(1→6) linkages but has no detectable sequence similarity to that of group D2, which confers the same linkage. We find the remnant of a D3-like wzy gene in the O-antigen gene clusters of groups D1 and B and suggest that this is the original wzy gene of these O-antigen gene clusters.

  gene, O-antigen, O antigen, group, cluster, gene cluster, Salmonella, Salmonella enterica, relationship

  NCBI PubMed ID: 9473060
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: reeves@angis.usyd.edu.au
  Institutions: Department of Microbiology, The University of Sydney,Australia
  
   
  
  Salmonella enterica D2 (O9), Salmonella enterica D3 (O9), Salmonella enterica O27, Salmonella enterica O46
  CSDB ID 6612 (all data & tools)
• Article ID: 1778
  Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" - Biochemistry (Moscow) 59(12) (1994) 1325-1383
  

  This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.

  structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1

  NCBI PubMed ID: 7533007
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Salmonella zuerich D3
  CSDB ID 108613 (all data & tools)
• Article ID: 3847
  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?BUS2-0016-0014
  Publisher: Polish Chemical Society
  Correspondence: jerzyg@chemik.chem.univ.gda.pl
  Institutions: Wydzial Chemii, Uniwersytet Gdanski, ul. Sobieskiego 18, 80-952 Gdansk
  
   
  
  Salmonella haarlem D2 (O9,46)
  CSDB ID 25617 (all data & tools)
• Article ID: 4315
  Hong Y, Cunneen MM, Reeves PR "The Wzx translocases for Salmonella enterica O-antigen processing have unexpected serotype specificity" - Molecular Microbiology 84(4) (2012) 620-630
  

  Most Gram-negative bacteria have an O antigen, a polysaccharide with many repeats of a short oligosaccharide that is a part of the lipopolysaccharide, the major lipid in the outer leaflet of the outer membrane. Lipopolysaccharide is variable with 46 forms in Salmonella enterica that underpin the serotyping scheme. Repeat units are assembled on a lipid carrier that is embedded in the cell membrane, and are then translocated by the Wzx translocase from the cytoplasmic face to the outer face of the cell membrane, followed by polymerization. The O antigen is then incorporated into lipopolysaccharide and exported to the outer membrane. The Wzx translocase is widely thought to be specific only for the first sugar of the repeat unit, despite extensive variation in both O antigens and Wzx translocases. However, we found for S. enterica groups B, D2 and E that Wzx translocation exhibits significant specificity for the repeat-unit structure, as variants with single sugar differences are translocated with lower efficiency and little long-chain O antigen is produced. It appears that Wzx translocases are specific for their O antigen for normal levels of translocation.

  O-antigen, Salmonella enterica, wzx

  NCBI PubMed ID: 22497246
  Publication DOI: 10.1111/j.1365-2958.2012.08048.x
  Journal NLM ID: 8712028
  Publisher: 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
  
   
  
  Salmonella enterica D2
  CSDB ID 28395 (all data & tools)
• Article ID: 4329
  Knirel YA "Structure of O-antigens" - Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
  

  The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.

  Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis

  Publication DOI: 10.1007/978-3-7091-0733-1_3
  Publisher: Springer
  Correspondence: knirel@ioc.ac.ru
  Editors: Knirel YA, Valvano MA
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Salmonella enterica II O9,46
  CSDB ID 27414 (all data & tools)
• Article ID: 4683
  Hong Y, Reeves PR "Diversity of O-antigen repeat unit structures can account for the substantial sequence variation of Wzx translocases" - Journal of Bacteriology 196(9) (2014) 1713-1722
  

  The most common system for synthesis of cell surface polysaccharides is the Wzx/Wzy-dependent pathway, which involves synthesis, on the cytoplasmic face of the cell membrane, of repeat units, which are then translocated to the periplasmic face by a Wzx translocase and then polymerized by Wzy to generate the polysaccharide. One such polysaccharide is O antigen, which is incorporated into lipopolysaccharide (LPS). The O antigen is extremely variable, with over 186 forms in Escherichia coli. Wzx proteins are also very diverse, but they have been thought to be specific only for the first sugar of the repeat units. However, recent studies demonstrated examples in which Wzx translocases have considerable preference for their native repeat unit, showing that specificity can extend well beyond the first sugar. These results appear to be in conflict with the early conclusions, but they involved specificity for side branch residues and could be a special case. Here we take six Wzx translocases that were critical in the earlier studies on the importance of the first sugar and assess their ability to translocate the Escherichia coli O16 and O111 repeat units. We use gene replacements to optimize maintenance of expression level and show that under these conditions the native translocases are the most effective for their native repeat unit, being, respectively, 64-fold and 4-fold more effective than the next best. We conclude that Wzx translocases are commonly adapted to their native repeat unit, which provides an explanation for the great diversity of wzx genes.

  Lipopolysaccharide, structure, polysaccharide, O-antigen, Escherichia coli, specificity, Cell Membrane, membrane, surface polysaccharide, diversity

  Publication DOI: 10.1128/JB.01323-13
  Journal NLM ID: 2985120R
  Publisher: 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
  
   
  
  Salmonella enterica D2
  CSDB ID 30274 (all data & tools)
• Article ID: 4759
  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: 25987464
  Publication DOI: 10.1099/mic.0.000113
  Journal NLM ID: 0376646
  Publisher: 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
  
   
  
  Salmonella enterica D2
  CSDB ID 30906 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136105,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_139420,IEDB_139421,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_7,SB_72

• Article ID: 357
  Rahman MM, Guard-Petter J, Carlson RW "A virulent isolate of Salmonella enteritidis produces a Salmonella typhi-like lipopolysaccharide" - Journal of Bacteriology 179(7) (1997) 2126-2131
  

  The lipopolysaccharide (LPS) of Salmonella enteritidis has been implicated as a virulence factor of this organism. Therefore, the LPS from a stable virulent isolate, SE6-E21, was compared with that from an avirulent isolate, SE6-E5. The LPSs were extracted, and the high-molecular-weight (HMW) LPS was separated from the low-molecular-weight (LMW) LPS for both isolates. Both the HMW and LMW LPSs were characterized by glycosyl composition and linkage analyses. Immunochemical characterization was performed by Western blotting using factor 9 antiserum and using S. typhimurium antiserum which contains factors 1, 4, 5, and 12(2). In addition, the polysaccharides released by mild acid hydrolysis were isolated and subjected to hydrolysis by bacteriophage P22, which contains endorhamnosidase activity. The resulting oligosaccharides were purified by using Bio-Gel P4 gel permeation chromatography and characterized by nuclear magnetic resonance spectroscopy, fast atom bombardment mass spectrometry (FAB-MS), tandem MS-MS, and matrix-assisted laser desorption time of flight MS. The results show that the HMW LPS O-antigen polysaccharides from both isolates are comprised of two different repeating units, -[→2)-[α-Tyvp-(1→3)]β-D-Manp-(1→4)-α-L-Rhap-(1→3)-α-D-Galp-(1→]- (structure I) and [→2)-[α-Tyvp-(1→3)]β-D-Manp-(1→4)-α-L-Rhap-(1→3)-[α-D-Glcp-(1→4)]α-D-Galp-(1→]- (structure II). The LMW LPSs from both isolates contains truncated O-antigen polysaccharide which is comprised of only structure I. In the virulent SE6-E21 isolate, the HMW LPS has a structure I/II ratio of 1:1, while in the avirulent SE6-E5 isolate, this ratio is 7:1. While the 7:1 ratio represents the published level of glucosylation for S. enteritidis LPS as well as for S. enteritidis LPS purchased from Sigma Chemical Co., the 1:1 ratio found for the virulent SE6-E21 is identical to the high level of glucosylation reported for S. typhi LPS. Thus, the LPS from the virulent SE6-E21 isolate produces an S. typhi-like LPS. Furthermore, the amount of O-antigen polysaccharide in SE6-E21 was twice that in SE6-E5.

  Lipopolysaccharide, LPS, isolate, Salmonella, Salmonella enteritidis, virulent

  NCBI PubMed ID: 9079895
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: RCARLSON@ccrc.uga.edu
  Institutions: Complex Carbohydrate Research Center, The University of Georgia, Athens, GA, USA, Southeast Poultry Research Laboratory, Agricultural Research Service, U.S. Department of Agriculture, Athens, Georgia 306052
  Methods: NMR, MS, composition analysis, immunochemical methods, linkage analysis
  
   
  
  Salmonella enteritidis SE6-E21
  CSDB ID 8043 (all data & tools)
• Article ID: 5094
  Li P, Liu Q, Luo H, Liang K, Yi J, Luo Y, Hu Y, Han Y, Kong Q "O-Serotype Conversion in Salmonella Typhimurium Induces Protective Immune Responses against Invasive Non-Typhoidal Salmonella Infections" - Frontiers in Immunology 8 (2017) 1647
  

  Salmonella infections remain a big problem worldwide, causing enteric fever by Salmonella Typhi (or Paratyphi) or self-limiting gastroenteritis by non-typhoidal Salmonella (NTS) in healthy individuals. NTS may become invasive and cause septicemia in elderly or immuno-compromised individuals, leading to high mortality and morbidity. No vaccines are currently available for preventing NTS infection in human. As these invasive NTS are restricted to several O-antigen serogroups including B1, D1, C1, and C2, O-antigen polysaccharide is believed to be a good target for vaccine development. In this study, a strategy of O-serotype conversion was investigated to develop live attenuated S. Typhimurium vaccines against the major serovars of NTS infections. The immunodominant O4 serotype of S. Typhimurium was converted into O9, O7, and O8 serotypes through unmarked chromosomal deletion-insertion mutations. O-serotype conversion was confirmed by LPS silver staining and western blotting. All O-serotype conversion mutations were successfully introduced into the live attenuated S. Typhimurium vaccine S738 (Δcrp Δcya) to evaluate their immunogenicity in mice model. The vaccine candidates induced high amounts of heterologous O-polysaccharide-specific functional IgG responses. Vaccinated mice survived a challenge of 100 times the 50% lethality dose (LD50) of wild-type S. Typhimurium. Protective efficacy against heterologous virulent Salmonella challenges was highly O-serotype related. Furthermore, broad-spectrum protection against S. Typhimurium, S. Enteritidis, and S. Choleraesuis was observed by co-vaccination of O9 and O7 O-serotype-converted vaccine candidates. This study highlights the strategy of expressing heterologous O-polysaccharides via genetic engineering in developing live attenuated S. Typhimurium vaccines against NTS infections.

  O-antigen, cross-protection, S. Choleraesuis, S. Enteritidis, S. Newport, S. Typhimurium, live attenuated Salmonella vaccine

  NCBI PubMed ID: 29255460
  Publication DOI: 10.3389/fimmu.2017.01647
  Journal NLM ID: 101560960
  Publisher: Lausanne: Frontiers Research Foundation
  Correspondence: kongqiki@163.com
  Institutions: Institute of Preventive Veterinary Medicine, College of Veterinary Medicine, Sichuan Agricultural University, Chengdu, China, Center for Infectious Diseases and Vaccinology, The Biodesign Institute, Arizona State University, Tempe, AZ, United States, College of Animal Science and Technology, Southwest University, Chongqing, China, Department of Infectious Diseases and Pathology, University of Florida, Gainesville, FL, United States
  Methods: SDS-PAGE, DNA techniques, ELISA, Western blotting, biological assays, serological methods, genetic methods, statistical analysis, motility assays
  
   
  
  Salmonella enterica ssp. enterica sv. Enteritidis O9 (D1)
  CSDB ID 12414 (all data & tools)
• Article ID: 6211
  Del Bino L, Osterlid KE, Wu DY, Nonne F, Romano MR, Codée J, Adamo R "Synthetic Glycans to Improve Current Glycoconjugate Vaccines and Fight Antimicrobial Resistance" - Chemical Reviews 122(20) (2022) 15672-15716
  

  Antimicrobial resistance (AMR) is emerging as the next potential pandemic. Different microorganisms, including the bacteria Acinetobacter baumannii, Clostridioides difficile, Escherichia coli, Enterococcus faecium, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, non-typhoidal Salmonella, and Staphylococcus aureus, and the fungus Candida auris, have been identified by the WHO and CDC as urgent or serious AMR threats. Others, such as group A and B Streptococci, are classified as concerning threats. Glycoconjugate vaccines have been demonstrated to be an efficacious and cost-effective measure to combat infections against Haemophilus influenzae, Neisseria meningitis, Streptococcus pneumoniae, and, more recently, Salmonella typhi. Recent times have seen enormous progress in methodologies for the assembly of complex glycans and glycoconjugates, with developments in synthetic, chemoenzymatic, and glycoengineering methodologies. This review analyzes the advancement of glycoconjugate vaccines based on synthetic carbohydrates to improve existing vaccines and identify novel candidates to combat AMR. Through this literature survey we built an overview of structure-immunogenicity relationships from available data and identify gaps and areas for further research to better exploit the peculiar role of carbohydrates as vaccine targets and create the next generation of synthetic carbohydrate-based vaccines.

  carbohydrates, glycan, glycoconjugate vaccine

  NCBI PubMed ID: 35608633
  Publication DOI: 10.1021/acs.chemrev.2c00021
  Journal NLM ID: 2985134R
  Publisher: Chem Rev
  Correspondence: J. Codée ; R. Adamo
  Institutions: GSK, R&D, 53100 Siena, Italy, Leiden Institute of Chemistry, Leiden University, 2300 RA Leiden, The Netherlands
  
   
  
  Salmonella enterica ssp. enterica sv. Enteritidis
  CSDB ID 20913 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136105,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_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_7,SB_72

• Article ID: 357
  Rahman MM, Guard-Petter J, Carlson RW "A virulent isolate of Salmonella enteritidis produces a Salmonella typhi-like lipopolysaccharide" - Journal of Bacteriology 179(7) (1997) 2126-2131
  

  The lipopolysaccharide (LPS) of Salmonella enteritidis has been implicated as a virulence factor of this organism. Therefore, the LPS from a stable virulent isolate, SE6-E21, was compared with that from an avirulent isolate, SE6-E5. The LPSs were extracted, and the high-molecular-weight (HMW) LPS was separated from the low-molecular-weight (LMW) LPS for both isolates. Both the HMW and LMW LPSs were characterized by glycosyl composition and linkage analyses. Immunochemical characterization was performed by Western blotting using factor 9 antiserum and using S. typhimurium antiserum which contains factors 1, 4, 5, and 12(2). In addition, the polysaccharides released by mild acid hydrolysis were isolated and subjected to hydrolysis by bacteriophage P22, which contains endorhamnosidase activity. The resulting oligosaccharides were purified by using Bio-Gel P4 gel permeation chromatography and characterized by nuclear magnetic resonance spectroscopy, fast atom bombardment mass spectrometry (FAB-MS), tandem MS-MS, and matrix-assisted laser desorption time of flight MS. The results show that the HMW LPS O-antigen polysaccharides from both isolates are comprised of two different repeating units, -[→2)-[α-Tyvp-(1→3)]β-D-Manp-(1→4)-α-L-Rhap-(1→3)-α-D-Galp-(1→]- (structure I) and [→2)-[α-Tyvp-(1→3)]β-D-Manp-(1→4)-α-L-Rhap-(1→3)-[α-D-Glcp-(1→4)]α-D-Galp-(1→]- (structure II). The LMW LPSs from both isolates contains truncated O-antigen polysaccharide which is comprised of only structure I. In the virulent SE6-E21 isolate, the HMW LPS has a structure I/II ratio of 1:1, while in the avirulent SE6-E5 isolate, this ratio is 7:1. While the 7:1 ratio represents the published level of glucosylation for S. enteritidis LPS as well as for S. enteritidis LPS purchased from Sigma Chemical Co., the 1:1 ratio found for the virulent SE6-E21 is identical to the high level of glucosylation reported for S. typhi LPS. Thus, the LPS from the virulent SE6-E21 isolate produces an S. typhi-like LPS. Furthermore, the amount of O-antigen polysaccharide in SE6-E21 was twice that in SE6-E5.

  Lipopolysaccharide, LPS, isolate, Salmonella, Salmonella enteritidis, virulent

  NCBI PubMed ID: 9079895
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: RCARLSON@ccrc.uga.edu
  Institutions: Complex Carbohydrate Research Center, The University of Georgia, Athens, GA, USA, Southeast Poultry Research Laboratory, Agricultural Research Service, U.S. Department of Agriculture, Athens, Georgia 306052
  Methods: NMR, MS, composition analysis, immunochemical methods, linkage analysis
  
   
  
  Salmonella enteritidis SE6-E5
  CSDB ID 8114 (all data & tools)
• Article ID: 4990
  De Benedetto G, Alfini R, Cescutti P, Caboni M, Lanzilao L, Necchi F, Saul A, Maclennan CA, Rondini S, Micoli F "Characterization of O-antigen delivered by Generalized Modules for Membrane Antigens (GMMA) vaccine candidates against nontyphoidal Salmonella" - Vaccine 35(3) (2017) 419-426
  

  Invasive nontyphoidal Salmonella disease (iNTS) is a leading cause of death and morbidity in Africa. The most common pathogens are Salmonella enterica serovars Typhimurium and Enteritidis. The O-antigen portion of their lipopolysaccharide is a target of protective immunity and vaccines targeting O-antigen are currently in development. Here we investigate the use of Generalized Modules for Membrane Antigens (GMMA) as delivery system for S. Typhimurium and S. Enteritidis O-antigen. Gram-negative bacteria naturally shed outer membrane in a blebbing process. By deletion of the tolR gene, the level of shedding was greatly enhanced. Further genetic modifications were introduced into the GMMA-producing strains in order to reduce reactogenicity, by detoxifying the lipid A moiety of lipopolysaccharide. We found that genetic mutations can impact on expression of O-antigen chains. All S. Enteritidis GMMA characterized had an O-antigen to protein w/w ratio higher than 0.6, while the ratio was 0.7 for S. Typhimurium ∆tolR GMMA, but decreased to less than 0.1 when further mutations for lipid A detoxification were introduced. Changes were also observed in O-antigen chain length and level and/or position of O-acetylation. When tested in mice, the GMMA induced high levels of anti-O-antigen-specific IgG functional antibodies, despite variation in density and O-antigen structural modifications. In conclusion, simplicity of manufacturing process and low costs of production, coupled with encouraging immunogenicity data, make GMMA an attractive strategy to further investigate for the development of a vaccine against iNTS.

  O-antigen, Salmonella typhimurium, vaccine, Salmonella enteritidis, GMMA, Outer membrane vesicles

  Publication DOI: 10.1016/j.vaccine.2016.11.089
  Journal NLM ID: 8406899
  Publisher: Elsevier
  Correspondence: francesca.x.micoli@gsk.com
  Institutions: Dipartimento di Scienze della Vita, Ed. C11, Universita degli Studi di Trieste, via L. Giorgieri 1, 34127 Trieste, Italy, Antimicrobial Discovery Center, Department of Biology, Boston, MA, USA, Jenner Institute, Nuffield Department of Medicine, University of Oxford, Old Road Campus Research Building, Roosevelt Drive, Oxford OX3 7DQ, UK, GSK Vaccines Institute for Global Health (GVGH) S.r.l. (former Novartis Vaccines Institute for Global Health, NVGH), Via Fiorentina 1, 53100 Siena, Italy
  Methods: SDS-PAGE, MALDI-MS, serological methods, HPAEC-PAD, immunization, immunogenicity in mice, HPLC-SEC/MALS
  
   
  
  Salmonella enterica sv. Enteritidis O9
  CSDB ID 12076 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Aglycon: #3,4,3_aXTyvp // #3,4_bDManp // #3_aLRhap // #_aDGalp //
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_136105,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_139420,IEDB_139421,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_7,SB_72

• Article ID: 1281
  Szafranek J, Gajdus J, Kaczyński Z, Dziadziuszko H, Kunikowska D, Glosnicka R, Yoshida T, Vihanto J, Pihlaja K "Immunological and chemical studies of Salmonella haarlem somatic antigen epitopes. I. Structural studies of O-antigen" - FEMS Immunology and Medical Microbiology 21(4) (1998) 243-252
  

  Lipopolysaccharide (LPS) of Salmonella haarlem was hydrolyzed and the products separated. The structure of the O-specific polysaccharide (OPS) was found from sugar and methylation analyses. Rhamnose, mannose, galactose and tyvelose were detected and their linkage modes were established. The structure was confirmed by 1H, homonuclear and heteronuclear correlations and 13C NMR spectra. Anomeric configurations were assigned by chromium trioxide oxidation and proton coupled 13C spectra. Sugar sequence was established from specific carbon shift data and nuclear Overhauser effect spectroscopy. The repeating unit structure of S. haarlem OPS as →3)-α-D-Galp-(1→6)-[α-Tyvp-(1→3)]-β-D-Manp-(1→4)-α-L-Rhap was estimated. No structural heterogeneity of the antigen was found.

  Lipopolysaccharide, antigen, structure, structural, O-antigen, O antigen, epitope, immunological, epitopes, O-polysaccharide, Salmonella, chemical, nuclear magnetic resonance, structural studies, somatic, antigen epitope

  NCBI PubMed ID: 9752996
  Journal NLM ID: 9315554
  Publisher: Elsevier
  Correspondence: janat+AEA-chemik.chem.univ.gda.pl
  Institutions: Department of Chemistry, University of Gdansk, Gdansk, Poland, Institute of Maritime and Tropical Medicine, Powstania Styczniowego Str., 9b, 81-519 Gdynia, Poland, Polymer Science Department, Hokkaido University, Kita-10 Nishi-8, Kita-ku, Sapporo 060, Japan, Department of Chemistry, University of Turku, FIN-200500 Turku, Finland
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, NMR, chromium trioxide oxidation
  
   
  
  Salmonella haarlem
  CSDB ID 4985 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136105,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_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_7,SB_72

• Article ID: 1778
  Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" - Biochemistry (Moscow) 59(12) (1994) 1325-1383
  

  This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.

  structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1

  NCBI PubMed ID: 7533007
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Salmonella strasbourg D2, Salmonella zuerich D3
  CSDB ID 108611 (all data & tools)
• Article ID: 3847
  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?BUS2-0016-0014
  Publisher: Polish Chemical Society
  Correspondence: jerzyg@chemik.chem.univ.gda.pl
  Institutions: Wydzial Chemii, Uniwersytet Gdanski, ul. Sobieskiego 18, 80-952 Gdansk
  
   
  
  Salmonella strasbourg D2 (O9,46)
  CSDB ID 25616 (all data & tools)

Show legend Show as text

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

• Article ID: 2893
  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: 5360616
  Publication DOI: 10.3891/acta.chem.scand.23-1588
  Journal NLM ID: 0421263
  Publisher: 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
  
   
  
  Salmonella enteritidis I.S.64, Salmonella typhi I.S.59
  CSDB ID 100067 (all data & tools)

Show legend Show as text

Structure type: structural motif or average structure
Compound class: LPS
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136044,IEDB_136095,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_1394181,IEDB_1394182,IEDB_139420,IEDB_139421,IEDB_141794,IEDB_141798,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88

• Article ID: 3093
  Pappas RS, Sweetman BJ, Ray S, Hellerqvist CG "Monomer sequence determination of carbohydrates using fast-atom bombardment mass spectrometry of periodate-oxidized acetate ester derivatives" - Carbohydrate Research 197 (1990) 1-14
  

  A derivatization method, adapted from that of Angel et al. (ref. 10), for sequencing sugar residues in partially degraded poly- and oligo-saccharides using positive-ion f.a.b.-m.s. is described. Derivative selection provides sequence information by directing fragmentation exclusively to both sides of glycosidic oxygen atoms and, in the case of opened rings, between glycosidic carbon and ring oxygen atoms. Polysaccharides or oligosaccharides are subjected to sequential periodate oxidation, borodeuteride reduction, and acetylation. The derivatized polysaccharides are then subjected to partial degradation, acetylation, and high-performance liquid chromatography (h.p.l.c.) purification. F.a.b.-m.s. data obtained on model compounds, using 3-nitrobenzyl alcohol as matrix for f.a.b.-m.s., demonstrated direction of fragmentation to both sides of the glycosidic oxygen atom in unoxidized residues, and to both sides of the acetal oxygen atoms in oxidized residues. Oligosaccharide linkage and sequence may thus be determined by observing fragmentation from both the reducing and non-reducing ends of the molecule. Two Salmonella lipopolysaccharides, derivatized by this procedure, were partially hydrolyzed and then acetylated. Analysis of the h.p.l.c.-purified oligosaccharide derivatives by f.a.b.-m.s. demonstrated the applicability of the technique for sequencing nmol quantities of branched structures.

  Publication DOI: 10.1016/0008-6215(90)84125-E
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Department of Biochemistry, Vanderbilt University, School of Medicine Nashville, Tennessee 37232, USA
  Methods: FAB-MS, HPLC
  
   
  
  Salmonella strasbourg
  CSDB ID 115841 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_1394181,IEDB_1394182,IEDB_139420,IEDB_139421,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_7,SB_72,SB_88

• Article ID: 3635
  Fukuda M, Egami F, Hammerling G, Luderitz O, Bagdian G, Staub AM "A reinvestigation of the anomeric configuration of mannose in the antigens of Salmonella groups B, D and E" - European Journal of Biochemistry 20(3) (1971) 438-441
  

  The anomeric configuration of mannose is a in the 0 antigens of Salmonella groups Band D, and b in group E, i.e. directly opposite to what was anticipated earlier from data obtained with mannosidase from rat epididymis. The present results were obtained with the aid of a-mannosidase from jack bean meal and of purified a- and b-mannosidases from a marine gastropod, which were allowed to act upon the disaccharides mannosyl-rhamnose isolated from partial hydrolysates of the respective antigens. The new findings, however, do not alter the validity of previous conclusions.

  antigen, chemistry, analysis, group, antigens, immunology, Salmonella, Salmonella typhimurium, chromatography, Mannose, configuration, reinvestigation, anomeric, anomeric configuration, Glycoside Hydrolases, D, Mollusca, Plant Extracts

  NCBI PubMed ID: 4931954
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Institutions: Department of Biophysics and Biochemistry, Faculty of Science, Univwersity of Tokyo.
  Methods: biochemical methods
  
   
  
  Salmonella strasbourg D2
  CSDB ID 29901 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_139420,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

• Article ID: 3847
  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?BUS2-0016-0014
  Publisher: Polish Chemical Society
  Correspondence: jerzyg@chemik.chem.univ.gda.pl
  Institutions: Wydzial Chemii, Uniwersytet Gdanski, ul. Sobieskiego 18, 80-952 Gdansk
  
   
  
  Salmonella zuerich D3 (O1,9,24,46)
  CSDB ID 25618 (all data & tools)
• Article ID: 4759
  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: 25987464
  Publication DOI: 10.1099/mic.0.000113
  Journal NLM ID: 0376646
  Publisher: 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
  
   
  
  Salmonella enterica D3
  CSDB ID 30907 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136105,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_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_7,SB_72

• Article ID: 3847
  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?BUS2-0016-0014
  Publisher: Polish Chemical Society
  Correspondence: jerzyg@chemik.chem.univ.gda.pl
  Institutions: Wydzial Chemii, Uniwersytet Gdanski, ul. Sobieskiego 18, 80-952 Gdansk
  
   
  
  Salmonella zuerich D3 (O1,9,24,46)
  CSDB ID 25619 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136105,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_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_7,SB_72

• Article ID: 4329
  Knirel YA "Structure of O-antigens" - Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
  

  The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.

  Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis

  Publication DOI: 10.1007/978-3-7091-0733-1_3
  Publisher: Springer
  Correspondence: knirel@ioc.ac.ru
  Editors: Knirel YA, Valvano MA
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Salmonella enterica ssp. enterica sv. Strasbourg O9,46
  CSDB ID 27413 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136105,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_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_7,SB_72

• Article ID: 4329
  Knirel YA "Structure of O-antigens" - Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
  

  The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.

  Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis

  Publication DOI: 10.1007/978-3-7091-0733-1_3
  Publisher: Springer
  Correspondence: knirel@ioc.ac.ru
  Editors: Knirel YA, Valvano MA
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Salmonella enterica II O9,46,27
  CSDB ID 27415 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-antigen
Contained glycoepitopes: IEDB_136105,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_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_7,SB_72

• Article ID: 4355
  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: 23142430
  Publication DOI: 10.1016/j.ab.2012.10.038
  Journal NLM ID: 0370535
  Publisher: 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
  
   
  
  Salmonella enteritidis O9
  CSDB ID 28462 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136105,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_139420,IEDB_139421,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_36,SB_44,SB_7,SB_72

• Article ID: 4533
  Hong Y, Duda KA, Cunneen MM, Holst O, Reeves PR "The WbaK acetyltransferase of Salmonella enterica group E gives insights into O antigen evolution" - Microbiology (2013) 2316-2322
  

  O antigens are polysaccharides consisting of repeat units of three to six sugars, generally assembled by genes in a discrete O antigen gene cluster. Salmonella enterica produces 46 forms of O antigen, and most of the variation is determined by genes in the gene cluster. However in some cases the structures are modified by enzymes encoded outside of the gene cluster, and several such modifications have been reported for Salmonella enterica group E, some on bacteriophages and one at a distant chromosomal site. We identified the enzyme, WbaK, that is responsible for O-acetylating the subgroup E1 O antigen, and find that the gene is located just downstream of the gene cluster as currently known. The wbaK gene appears to have been imported by a recombination event that also replaced the last 37 bp of the wbaP gene, indicating that homologous recombination was involved. Some of the group E strains we have must have the original gene cluster, as they lack wbaK and their downstream end is very similar to those for several other Salmonella enterica O antigens. In effect the gene cluster was extended by one gene. It appears that a function that is usually encoded by a gene outside of the gene cluster has been added to the gene cluster, in this case giving an example of how such gene clusters can evolve.

  structure, O-antigen, gene cluster, Genes, modification, Salmonella enterica, acetyltransferase, evolution, WbaK

  NCBI PubMed ID: 24014662
  Publication DOI: 10.1099/mic.0.069823-0
  Journal NLM ID: 0376646
  Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
  Correspondence: Peter R. Reeves
  Institutions: School of Molecular Bioscience, University of Sydney, New South Wales 2006, Australia, Division of Structural Biochemistry, Research Center Borstel, Leibniz-Center for Medicine and Biosciences, Airway Research Center North (ARCN), German Center for Lung Research (DZL), D-23845 Borstel, Germany
  Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, NMR-1D, immunoblotting, bioinformatic analysis
  
   
  
  Salmonella enterica ssp. enterica sv. Strasbourg (M2900)
  CSDB ID 29198 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: O-antigen repeat units
Compound class: O-antigen
Contained glycoepitopes: IEDB_136105,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_139420,IEDB_139421,IEDB_141794,IEDB_144983,IEDB_145001,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_7,SB_72

• Article ID: 4536
  Islam ST, Lam JS "Wzx flippase-mediated membrane translocation of sugar polymer precursors in bacteria" - Environmental Microbiology 15(4) (2013) 1001-1015
  

  Bacterial cell surface polysaccharides confer resistance to external stress and promote survival in biotic and abiotic environments. Glycan assembly often occurs at the periplasmic leaflet of the inner membrane (IM) from undecaprenyl pyrophosphate (UndPP)-linked polysaccharide units via the Wzx/Wzy-dependent pathway. Wzx is an integral IM protein found in Gram-negative and Gram-positive bacteria that mediates IM translocation of UndPP-linked sugar repeats from the cytoplasmic to the periplasmic leaflet; interaction of Wzx with other assembly proteins is indirectly supported by genetic evidence. Topological mapping has indicated 12 alpha-helical transmembrane segments (TMS), with the number of charged TMS residues fluctuating based on the mapping method used. A novel Wzx tertiary structure model has been built, allowing for substrate-binding or energy-coupling roles to be proposed for functionally important charged and aromatic TMS residues. It has also led to a proposed antiport-like mechanism of Wzx function. Exquisite substrate specificity of Wzx proteins was recently revealed in distinguishing between UndPP-linked substrates with identical main-chain sugar repeats, but differing in the chemical composition of a terminal sugar side-branch cap. The objective of this review is to synthesize the most up-to-date knowledge concerning Wzx flippases and to provide perspective for future investigations in this burgeoning field.

  structure, polysaccharide, interaction, Gram-negative, surface polysaccharide, Gram-positive, mapping, gram-positive bacteria, Wzx flippases, Wzx/Wzy

  NCBI PubMed ID: 23016929
  Publication DOI: 10.1111/j.1462-2920.2012.02890.x
  Journal NLM ID: 100883692
  Publisher: Blackwell Publishing
  Correspondence: Joseph S. Lam
  Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, ON, Canada, N1G 2W1
  
   
  
  Salmonella enterica D2
  CSDB ID 29565 (all data & tools)