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1. Compound ID: 202
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a-Tyvp-(1-3)-+
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-6)-b-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_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
The structure is contained in the following publication(s):
- 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: 9752996Journal NLM ID: 9315554Publisher: Elsevier
Correspondence: janat@chemik.chem.univ.gda.pl
Institutions: Department of Chemistry, University of Gdansk, Poland
Methods: Smith degradation
- Article ID: 1408
Curd H, Liu D, Reeves PR "Relationships among the O-antigen gene clusters of Salmonella enterica groups B, D1, D2, and D3" -
Journal of Bacteriology 180(4) (1998) 1002-1007
The O antigen is an important cell wall antigen of gram-negative bacteria, and the genes responsible for its biosynthesis are located in a gene cluster. We have cloned and sequenced the DNA segment unique to the O-antigen gene cluster of Salmonella enterica group D3. This segment includes a novel O-antigen polymerase gene (wzyD3). The polymerase gives α(1→6) linkages but has no detectable sequence similarity to that of group D2, which confers the same linkage. We find the remnant of a D3-like wzy gene in the O-antigen gene clusters of groups D1 and B and suggest that this is the original wzy gene of these O-antigen gene clusters.
gene, O-antigen, O antigen, group, cluster, gene cluster, Salmonella, Salmonella enterica, relationship
NCBI PubMed ID: 9473060Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: reeves@angis.usyd.edu.au
Institutions: Department of Microbiology, The University of Sydney,Australia
- Article ID: 1778
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 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?BUS2-0016-0014Publisher: Polish Chemical Society
Correspondence: jerzyg@chemik.chem.univ.gda.pl
Institutions: Wydzial Chemii, Uniwersytet Gdanski, ul. Sobieskiego 18, 80-952 Gdansk
- Article ID: 4315
Hong Y, Cunneen MM, Reeves PR "The Wzx translocases for Salmonella enterica O-antigen processing have unexpected serotype specificity" -
Molecular Microbiology 84(4) (2012) 620-630
Most Gram-negative bacteria have an O antigen, a polysaccharide with many repeats of a short oligosaccharide that is a part of the lipopolysaccharide, the major lipid in the outer leaflet of the outer membrane. Lipopolysaccharide is variable with 46 forms in Salmonella enterica that underpin the serotyping scheme. Repeat units are assembled on a lipid carrier that is embedded in the cell membrane, and are then translocated by the Wzx translocase from the cytoplasmic face to the outer face of the cell membrane, followed by polymerization. The O antigen is then incorporated into lipopolysaccharide and exported to the outer membrane. The Wzx translocase is widely thought to be specific only for the first sugar of the repeat unit, despite extensive variation in both O antigens and Wzx translocases. However, we found for S. enterica groups B, D2 and E that Wzx translocation exhibits significant specificity for the repeat-unit structure, as variants with single sugar differences are translocated with lower efficiency and little long-chain O antigen is produced. It appears that Wzx translocases are specific for their O antigen for normal levels of translocation.
O-antigen, Salmonella enterica, wzx
NCBI PubMed ID: 22497246Publication DOI: 10.1111/j.1365-2958.2012.08048.xJournal NLM ID: 8712028Publisher: Blackwell Publishing
Correspondence: peter.reeves@sydney.edu.au
Institutions: School of Molecular Bioscience, The University of Sydney, Sydney, NSW, Australia
Methods: SDS-PAGE, genetic methods
- Article ID: 4329
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 4683
Hong Y, Reeves PR "Diversity of O-antigen repeat unit structures can account for the substantial sequence variation of Wzx translocases" -
Journal of Bacteriology 196(9) (2014) 1713-1722
The most common system for synthesis of cell surface polysaccharides is the Wzx/Wzy-dependent pathway, which involves synthesis, on the cytoplasmic face of the cell membrane, of repeat units, which are then translocated to the periplasmic face by a Wzx translocase and then polymerized by Wzy to generate the polysaccharide. One such polysaccharide is O antigen, which is incorporated into lipopolysaccharide (LPS). The O antigen is extremely variable, with over 186 forms in Escherichia coli. Wzx proteins are also very diverse, but they have been thought to be specific only for the first sugar of the repeat units. However, recent studies demonstrated examples in which Wzx translocases have considerable preference for their native repeat unit, showing that specificity can extend well beyond the first sugar. These results appear to be in conflict with the early conclusions, but they involved specificity for side branch residues and could be a special case. Here we take six Wzx translocases that were critical in the earlier studies on the importance of the first sugar and assess their ability to translocate the Escherichia coli O16 and O111 repeat units. We use gene replacements to optimize maintenance of expression level and show that under these conditions the native translocases are the most effective for their native repeat unit, being, respectively, 64-fold and 4-fold more effective than the next best. We conclude that Wzx translocases are commonly adapted to their native repeat unit, which provides an explanation for the great diversity of wzx genes.
Lipopolysaccharide, structure, polysaccharide, O-antigen, Escherichia coli, specificity, Cell Membrane, membrane, surface polysaccharide, diversity
Publication DOI: 10.1128/JB.01323-13Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: peter.reeves@sydney.edu.au
Institutions: School of Molecular Bioscience (G08), University of Sydney, New South Wales, Australia
Methods: SDS-PAGE, genetic methods, cloning
- Article ID: 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: 25987464Publication DOI: 10.1099/mic.0.000113Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: peter.reeves@sydney.edu.au
Institutions: Department of Microbiology, University of Illinois, Urbana, IL 61801, USA, University of Illinois at Urbana-Champaign, School of Molecular Bioscience, Building D17, University of Sydney, NSW 2006, Australia
Methods: PCR, SDS-PAGE, DNA techniques, genetic methods
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2. Compound ID: 265
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a-Tyvp-(1-3)-+
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-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_174035,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 69
Falt IC, Mills D, Schweda EKH, Timmis KN, Lindberg AA "Construction of recombinant aroA salmonellae stably producing the Shigella dysenteriae serotype 1 O-antigen and structural characterization of the Salmonella/Shigella hybrid LPS" -
Microbial Pathogenesis 20(1) (1996) 11-30
The TN501 mercury resistant transposon containing the rfp and rfb loci encoding biosynthesis of the O-antigen of Shigella dysenteriae serotype 1 lipopolysaccharide (LPS) was constructed and introduced into aroA mutants of Salmonella typhimurium and Salmonella dublin. In five recombinant strains, both homologous LPS and hybrid LPS, consisting of Salmonella lipid A-core and Shigella O-antigen, were produced. All derivatives but one (SL3235) stably inherited the new trait. Immunofluorescence microscopy, using mixtures of differentially-labelled antibodies specific for either the Salmonella or the Shigella O-antigen, demonstrated that individual bacteria produced both types of LPS. Qualitative and quantitative analysis of polysaccharides obtained by mild hydrolysis of purified LPS was carried out by methylation analysis and NMR spectroscopy, and revealed that the ratio of Salmonella to Shigella O-antigen repeating units in the high molecular weight fraction of isolated polysaccharides varied from 1.3: 1 to 8.4:1 as based on the relative proportions of 1,4,5-tri-O-acetyl-2,3-di-O-methyl-L-rhamnitol (Salmonella repeating unit) and 1,3,5-tri-O-acetyl-2,4-di-O-methyl-L-rhamnitol (Shigella repeating unit). The attachment site of the Shigella O-antigen to the Salmonella core was investigated by construction of a mutant rfp-rfb gene cluster encoding the synthesis of only one repeat unit of the Shigella dysenteriae type 1 O-antigen, and its introduction into a rough Salmonella strain. This hybrid organism produced a polysaccharide with the following structure, [formula: see text] demonstrating that the Shigella dysenteriae type 1 O-antigen is linked at position O-4 of the subterminal D-glucose unit in the Salmonella core
LPS, Salmonella, Shigella dysenteriae type 1, hybrids, vaccine.
NCBI PubMed ID: 8692007Journal NLM ID: 8606191Publisher: Academic Press
Institutions: Department of Immunology, Microbiology, Pathology and Infectious Diseases, Karolinska Institute, Huddinge Hospital, Sweden, Department of Medical Biochemistry, University of Geneva, Switzerland, Division of Microbiology, National Research Centre for Biotechnology, Braunschweig, Germany, Clinical Research Centre, Karolinska Institute, Novum, Huddinge Hospital, Sweden
- Article ID: 1369
Baxa U, Steinbacher S, Miller S, Weintraub A, Huber R, Seckler R "Interactions of phage P22 tails with their cellular receptor, Salmonella O-antigen polysaccharide" -
Biophysical Journal 71 (1996) 2040-2048
Bacteriophage P22 binds to its cell surface receptor, the repetitive O-antigen structure in Salmonella lipopolysaccharide, by its six homotrimeric tailspikes. Receptor binding by soluble tailspikes and the receptor-inactivating endorhamnosidase activity of the tailspike protein were studied using octa- and dodecasaccharides comprising two and three O-antigen repeats of Salmonella enteritidis and Salmonella typhimurium lipopolysaccharides. Wild-type tailspike protein and three mutants (D392N, D395N, and E359Q) with defective endorhamnosidase activity were used. Oligosaccharide binding to all three subunits, measured by a tryptophan fluorescence quench or by fluorescence depolarization of a coumarin label attached to the reducing end of the dodecasaccharide, occurs independently. At 10 degrees C, the binding affinities of all four proteins to oligosaccharides from both bacterial strains are identical within experimental error, and the binding constants for octa- and dodecasaccharides are 1 x 10(6) M(-1) and 2 x 10(6) M(-1), proving that two O-antigen repeats are sufficient for lipopolysaccharide recognition by the tailspike. Equilibration with the oligosaccharides occurs rapidly, but the endorhamnosidase produces only one cleavage every 100 s at 10 degrees C or about 2 min(-1) at the bacterial growth temperature. Thus, movement of virions in the lipopolysaccharide layer before DNA injection may involve the release and rebinding of individual tailspikes rather than hydrolysis of the O-antigen.
polysaccharide, O-antigen, O antigen, Salmonella, interaction, cellular, receptor, phage
NCBI PubMed ID: 8889178Journal NLM ID: 0370626Publisher: Cambridge, MA: Cell Press
Correspondence: robert.seckler@biologie.uniregensburg.de
Institutions: Universitat Regensberg, Phusikalishe Biochemie, Regensberg, Germany
- Article ID: 1408
Curd H, Liu D, Reeves PR "Relationships among the O-antigen gene clusters of Salmonella enterica groups B, D1, D2, and D3" -
Journal of Bacteriology 180(4) (1998) 1002-1007
The O antigen is an important cell wall antigen of gram-negative bacteria, and the genes responsible for its biosynthesis are located in a gene cluster. We have cloned and sequenced the DNA segment unique to the O-antigen gene cluster of Salmonella enterica group D3. This segment includes a novel O-antigen polymerase gene (wzyD3). The polymerase gives α(1→6) linkages but has no detectable sequence similarity to that of group D2, which confers the same linkage. We find the remnant of a D3-like wzy gene in the O-antigen gene clusters of groups D1 and B and suggest that this is the original wzy gene of these O-antigen gene clusters.
gene, O-antigen, O antigen, group, cluster, gene cluster, Salmonella, Salmonella enterica, relationship
NCBI PubMed ID: 9473060Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: reeves@angis.usyd.edu.au
Institutions: Department of Microbiology, The University of Sydney,Australia
- Article ID: 1778
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 3244
Snyder DS, Gibson D, Heiss C, Kay W, Azadi P "Structure of a capsular polysaccharide isolated from Salmonella enteritidis" -
Carbohydrate Research 341(14) (2006) 2388-2397
Salmonella enteritidis is a food-borne enteric human pathogen that can form a complex protective extracellular matrix. We describe here a component of this matrix which is distinct from other known salmonella extracellular polysaccharides such as cellulose and colanic acid. We have used glycosyl composition and linkage analysis, as well as 1D and 2D NMR spectroscopy to determine the structure of this polysaccharide. We propose that the primary saccharide in the S. enteritidis capsule has a branched tetrasaccharide repeating unit having the following structure: →3)-α-D-Galp-(1→2)-[α-Tyvp-(1→3)]-α-D-Manp-(1→4)-α-L-Rhap-(1→. This structure is partially substituted on both tyvelose and galactose with a glucose-containing side chain. It further bears considerable similarity to the O antigen from this organism, a feature found in a number of other capsules from Gram-negative bacteria. In addition, we have detected fatty acids at levels that indicate the presence of a lipid anchor.
Extracellular matrix; Capsule; Salmonella; O Antigen; Capsular polysaccharide; Glycolipid
Publication DOI: 10.1016/j.carres.2006.06.010Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: azadi@ccrc.uga.edu
Institutions: Complex Carbohydrate Research Center, Athens, GA 30602-4712, USA, Department of Biochemistry and Microbiology, University of Victoria, Victoria, BC, Canada V8W 3P6
Methods: NMR, composition analysis, linkage analysis
- Article ID: 3285
Nnalue NA, Weintraub A, Oscarson S, Lindberg AA "Cross-reactivity between the mannan of Candida species, Klebsiella K24 polysaccharide and Salmonella C1 and E O-antigens is mediated by a terminal non-reducing b-mannosyl residue" -
European Journal of Biochemistry 220(3) (1994) 973-979
Rat monoclonal antibody MASC1-MR9 (MR9) binds to a mannan of Candida species and the O-antigenic polysaccharides of Salmonella bacteria of serogroups C1 (CO) and E (EO). Mannan and glycoconjugates comprising BSA and O-antigen polysaccharides, decasaccharide-BSA (CO-BSA) or trisaccharide-BSA (EO-BSA), inhibited each other's reactivity with MR9. The saccharides β-D-Manp-(1→6)-α-D-Manp-1-OMe, β-D-Manp(1→3)-α-D-Manp-1-OMe, β-D-Manp(1→2)-α-D-Manp-1-OMe (corresponds to the terminal non-reducing end of Salmonella serogroup C1 O-antigen) and β-D-Manp(1→4)-α-L-Rhap(1→3)-α-D-Galp-1-O-p-trifluoroacetamido aniline (corresponds to the backbone of Salmonella serogroup E O-antigen) inhibited the binding of MR9 to these antigens whereas α-D-Manp(1→3)-α-D-Manp-1-OMe and α-D-Manp(1→4)-α-L-Rhap-1-O-p-nitrophenyl did not. Saccharides (3-10 residues) of mammalian origin with terminal and internal Manp α-1→2, Manp α-1→3 and Manp α-1→6 residues also failed to inhibit at any concentration. None of the saccharides with internal β-mannosyl residue was able to inhibit the MR9 antibody. Monosaccharides D-mannose, β-D-Manp-1-OMe and 1,5 anhydro-D-mannitol inhibited the MR9 monoclonal antibody whereas α-D-Manp-1-OMe, β-D-Glcp-1-OMe, and β-D-Galp-1-OMe did not. In addition a Klebsiella K24 capsular polysaccharide containing a β-D-Manp(1→4)-α-D-GlcA (GlcA, glucuronic acid) as a structural element possessed an inhibitory activity. MR9 therefore recognizes an epitope within β-mannose monosaccharide residues at the terminal non-reducing ends of carbohydrate chains in mannan, and polysaccharides in Salmonella serogroups CO and EO and Klebsiella K24.
O-antigen, epitope, monoclonal antibodies, capsular polysaccharide, serogroup, Salmonella, Klebsiella, cross-reactivity, Candida
NCBI PubMed ID: 7511532Publication DOI: 10.1111/j.1432-1033.1994.tb18701.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Immunology, Microbiology, Pathology and Infectious Diseases, Karolinska Institute, Huddinge University Hospital, Sweden.
Methods: serological methods
- Article ID: 3602
Son S, Tano C, Furuike T, Sakairi N "Synthesis of a tetrasaccharide repeating unit of O-antigenic polysaccharide of Salmonella enteritidis by use of unique and odorless dodecyl thioglycosyl donors" -
Tetrahedron Letters 49(36) (2008) 5289-5292
The first total synthesis of a unique tetrasaccharide repeating unit of lipopolysaccharide from Salmonella enteritidis has been accomplished by assembly of dodecyl thioglycosides. The crucial key steps were preparation of a rare branched dideoxy sugar, dtyvelose (3,6-dideoxy-d-arabino-d-hexose) and sequential regioselective glycosylation at 2,3-positions of a central d-mannose residue 5 with d-tyvelose 6 and d-galactose donors 7.
synthesis, tetrasaccharide, O-antigenic polysaccharide, glycosylation, Salmonella enteritidis
Publication DOI: 10.1016/j.tetlet.2008.06.097Journal NLM ID: 2984819RPublisher: Elsevier
Correspondence: nsaka@ees.hokudai.ac.jp (N. Sakairi)
Institutions: Graduate School of Environmental Science, Hokkaido University, Kita-ku, Sapporo 060-0810, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, chemical synthesis, glycosylation
- Article ID: 3747
Olsson JD, Landstrom J, Ronnols J, Oscarson S, Widmalm G "Synthesis of and molecular dynamics simulations on a tetrasaccharide corresponding to the repeating unit of the capsular polysaccharide from Salmonella enteritidis" -
Organic and Biomolecular Chemistry 7(8) (2009) 1612-1618
Syntheses of two oligosaccharides as methyl glycosides related to the repeating unit of S. enteritidis capsular polysaccharide (CPS) are presented. The trisaccharide corresponds to the backbone of the CPS whereas the tetrasaccharide is a model for the repeating unit which has a branched structure. Molecular dynamics simulations investigating their flexibility and dynamics revealed that the oligosaccharides populate several conformational states and indicate that conformational averaging should be used in describing the accessible conformational space.
synthesis, capsular polysaccharide, conformational, molecular dynamics, Salmonella enteritidis
NCBI PubMed ID: 19343247Publication DOI: 10.1039/b823428kJournal NLM ID: 101154995Publisher: The Royal Society of Chemistry
Correspondence: G. Widmalm
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
Methods: 13C NMR, 1H NMR, chemical methods, MD simulations
- Article ID: 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?BUS2-0016-0014Publisher: Polish Chemical Society
Correspondence: jerzyg@chemik.chem.univ.gda.pl
Institutions: Wydzial Chemii, Uniwersytet Gdanski, ul. Sobieskiego 18, 80-952 Gdansk
- Article ID: 4315
Hong Y, Cunneen MM, Reeves PR "The Wzx translocases for Salmonella enterica O-antigen processing have unexpected serotype specificity" -
Molecular Microbiology 84(4) (2012) 620-630
Most Gram-negative bacteria have an O antigen, a polysaccharide with many repeats of a short oligosaccharide that is a part of the lipopolysaccharide, the major lipid in the outer leaflet of the outer membrane. Lipopolysaccharide is variable with 46 forms in Salmonella enterica that underpin the serotyping scheme. Repeat units are assembled on a lipid carrier that is embedded in the cell membrane, and are then translocated by the Wzx translocase from the cytoplasmic face to the outer face of the cell membrane, followed by polymerization. The O antigen is then incorporated into lipopolysaccharide and exported to the outer membrane. The Wzx translocase is widely thought to be specific only for the first sugar of the repeat unit, despite extensive variation in both O antigens and Wzx translocases. However, we found for S. enterica groups B, D2 and E that Wzx translocation exhibits significant specificity for the repeat-unit structure, as variants with single sugar differences are translocated with lower efficiency and little long-chain O antigen is produced. It appears that Wzx translocases are specific for their O antigen for normal levels of translocation.
O-antigen, Salmonella enterica, wzx
NCBI PubMed ID: 22497246Publication DOI: 10.1111/j.1365-2958.2012.08048.xJournal NLM ID: 8712028Publisher: Blackwell Publishing
Correspondence: peter.reeves@sydney.edu.au
Institutions: School of Molecular Bioscience, The University of Sydney, Sydney, NSW, Australia
Methods: SDS-PAGE, genetic methods
- Article ID: 4329
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 4477
Andres D, Gohlke U, Broeker NK, Schulze S, Rabsch W, Heinemann U, Barbirz S, Seckler R "An essential serotype recognition pocket on phage P22 tailspike protein forces Salmonella enterica serovar Paratyphi A O-antigen fragments to bind as non-solution conformers" -
Glycobiology 23(4) (2013) 486-494
Bacteriophage P22 recognizes O-antigen polysaccharides of Salmonella enterica subsp. enterica (S.) with its tailspike protein (TSP). In the serovars S. Typhimurium, S. Enteritidis, and S. Paratyphi A, the tetrasaccharide repeat units of the respective O-antigens consist of an identical main chain trisaccharide but different 3,6-dideoxyhexose substituents. Here, the epimers abequose, tyvelose, and paratose determine the specific serotype. P22TSP recognizes O-antigen octasaccharides in an extended binding site with a single 3,6-dideoxyhexose binding pocket. We have isolated S. Paratyphi A octasaccharides which were not available previously and determined the crystal structure of their complex with P22TSP. We discuss our data together with crystal structures of complexes with S. Typhimurium and S. Enteritidis octasaccharides determined earlier. Isothermal titration calorimetry (ITC) showed that S. Paratyphi A octasaccharide binds P22TSP less tightly, with a difference in binding free energy of approximately 7 kJ/mol at 20 degrees C compared to S. Typhimurium and S. Enteritidis octasaccharides. Individual protein-carbohydrate contacts were probed by amino acid replacements showing that the dideoxyhexose pocket contributes to binding of all three serotypes. However, S. Paratyphi A octasaccharides bind in a conformation with an energetically unfavorable varphi / psi glycosidic bond angle combination. By contrast, octasaccharides from the other serotypes bind as solution-like conformers. Two water molecules are conserved in all P22TSP complexes with octasaccharides of different serotypes. They line the dideoxyhexose binding pocket and force the S. Paratyphi A octasaccharides to bind as non-solution conformers. This emphasizes the role of solvent as part of carbohydrate binding sites.
Salmonella enterica, paratose, bacterial O-antigen, carbohydrate interaction, structural thermodynamics, tailspike protein
NCBI PubMed ID: 23292517Publication DOI: 10.1093/glycob/cws224Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: seckler@uni-potsdam.de; barbirz@uni-potsdam.de
Institutions: Physikalische Biochemie, Universitat Potsdam, Karl-Liebknecht-Str. 24-25, 14476 Potsdam, Germany
Methods: crystallography, thermodynamics, statistical analysis, crystallization, surface plasmon resonance (SPR), ITC
- Article ID: 4683
Hong Y, Reeves PR "Diversity of O-antigen repeat unit structures can account for the substantial sequence variation of Wzx translocases" -
Journal of Bacteriology 196(9) (2014) 1713-1722
The most common system for synthesis of cell surface polysaccharides is the Wzx/Wzy-dependent pathway, which involves synthesis, on the cytoplasmic face of the cell membrane, of repeat units, which are then translocated to the periplasmic face by a Wzx translocase and then polymerized by Wzy to generate the polysaccharide. One such polysaccharide is O antigen, which is incorporated into lipopolysaccharide (LPS). The O antigen is extremely variable, with over 186 forms in Escherichia coli. Wzx proteins are also very diverse, but they have been thought to be specific only for the first sugar of the repeat units. However, recent studies demonstrated examples in which Wzx translocases have considerable preference for their native repeat unit, showing that specificity can extend well beyond the first sugar. These results appear to be in conflict with the early conclusions, but they involved specificity for side branch residues and could be a special case. Here we take six Wzx translocases that were critical in the earlier studies on the importance of the first sugar and assess their ability to translocate the Escherichia coli O16 and O111 repeat units. We use gene replacements to optimize maintenance of expression level and show that under these conditions the native translocases are the most effective for their native repeat unit, being, respectively, 64-fold and 4-fold more effective than the next best. We conclude that Wzx translocases are commonly adapted to their native repeat unit, which provides an explanation for the great diversity of wzx genes.
Lipopolysaccharide, structure, polysaccharide, O-antigen, Escherichia coli, specificity, Cell Membrane, membrane, surface polysaccharide, diversity
Publication DOI: 10.1128/JB.01323-13Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: peter.reeves@sydney.edu.au
Institutions: School of Molecular Bioscience (G08), University of Sydney, New South Wales, Australia
Methods: SDS-PAGE, genetic methods, cloning
- Article ID: 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
- Article ID: 6383
Fontana C, Widmalm G "Primary Structure of Glycans by NMR Spectroscopy" -
Chemical Reviews 123(3) (2023) 1040-1102
Glycans, carbohydrate molecules in the realm of biology, are present as biomedically important glycoconjugates and a characteristic aspect is that their structures in many instances are branched. In determining the primary structure of a glycan, the sugar components including the absolute configuration and ring form, anomeric configuration, linkage(s), sequence, and substituents should be elucidated. Solution state NMR spectroscopy offers a unique opportunity to resolve all these aspects at atomic resolution. During the last two decades, advancement of both NMR experiments and spectrometer hardware have made it possible to unravel carbohydrate structure more efficiently. These developments applicable to glycans include, inter alia, NMR experiments that reduce spectral overlap, use selective excitations, record tilted projections of multidimensional spectra, acquire spectra by multiple receivers, utilize polarization by fast-pulsing techniques, concatenate pulse-sequence modules to acquire several spectra in a single measurement, acquire pure shift correlated spectra devoid of scalar couplings, employ stable isotope labeling to efficiently obtain homo- and/or heteronuclear correlations, as well as those that rely on dipolar cross-correlated interactions for sequential information. Refined computer programs for NMR spin simulation and chemical shift prediction aid the structural elucidation of glycans, which are notorious for their limited spectral dispersion. Hardware developments include cryogenically cold probes and dynamic nuclear polarization techniques, both resulting in enhanced sensitivity as well as ultrahigh field NMR spectrometers with a 1H NMR resonance frequency higher than 1 GHz, thus improving resolution of resonances. Taken together, the developments have made and will in the future make it possible to elucidate carbohydrate structure in great detail, thereby forming the basis for understanding of how glycans interact with other molecules.
NMR, glycan
NCBI PubMed ID: 36622423Publication DOI: 10.1021/acs.chemrev.2c00580Journal NLM ID: 2985134RPublisher: Chem Rev
Correspondence: G. Widmalm
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91 Stockholm, Sweden, Departamento de Química del Litoral, CENUR Litoral Norte, Universidad de la República, Paysandú 60000, Uruguay
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3. Compound ID: 1062
|
a-Tyvp-(1-3)-+ a-D-Glcp-(1-4)-+
| |
-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 310
Liu D, Lindqvist L, Reeves PR "Transferases of O-antigen biosynthesis in Salmonella enterica: Dideoxyhexosyltransferases of groups B and C2 and acetyltransferase of group C2" -
Journal of Bacteriology 177(14) (1995) 4084-4088
The O antigen is a polymer of oligosaccharide units. O antigens differ in their sugar composition and glycosidic linkages, and genes responsible for O-antigen-specific biosynthesis are grouped in the rfb gene cluster. In this study, we identified two abequosyltransferase genes and an acetyltransferase gene in Salmonella enterica groups B and C2 by in vitro assay and identified paratosyl-, tyvelosyl-, and abequosyltransferase genes from S. enterica groups A and D and Yersinia pseudotuberculosis serovar IIA, respectively, by comparison.
biosynthesis, O-antigen, transferase, Salmonella, Salmonella enterica, 3, 6-dideoxyhexose, acetyltransferase
NCBI PubMed ID: 7541787Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: reeves@angis.su.oz.au
Institutions: Department of Microbiology, University of Sydney, New South Wales 2006, Australia, and Department of Clinical Bacteriology, Huddinge Hospital, Karolinska Institute, S-141 86 Huddinge, Sweden.
- Article ID: 2516
Pokrovskii VV, Tregub AV, Tendetnik YY, Pokrovskii VI, Kochetkov NK, Chernyak AY, Levinskii AB "Immunobiological properties of synthetic antigen copolymers of synthetic O-determinants with acrylamide" -
Soviet Immunology = Immunologiya (1986) 46-50
Journal NLM ID: 8406555Publisher: New York, NY: Allerton Press
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4. Compound ID: 1140
|
a-Tyvp-(1-3)-a-D-6dmanHep-(1-4)-+
|
-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,SB_173,SB_7
The structure is contained in the following publication(s):
- Article ID: 345
Pacinelli E, Wang L, Reeves PR "Relationship of Yersinia pseudotuberculosis O antigens IA, IIA, and IVB: the IIA gene cluster was derived from that of IVB" -
Infection and Immunity 70(6) (2002) 3271-3276
O antigen is part of the lipopolysaccharide present in the outer membrane of gram-negative bacteria and is highly polymorphic. In this study, we obtained sequences of the O-antigen gene clusters for the Yersinia pseudotuberculosis antigens IA, IIA, and IVB. We propose that the IIA gene cluster was derived from the IVB cluster, one of the very few cases in which a parent gene cluster is identified, and that the IA gene cluster could be a hybrid of the IVB and IB gene clusters. All three O antigens contain 6-deoxy-D-mannoheptose, and we identified six genes for the biosynthetic pathway for the precursor of this sugar, GDP-6-deoxy-D-mannoheptose
O-antigen, antigens, gene cluster, Yersinia pseudotuberculosis, relationship, Yersinia
NCBI PubMed ID: 12011023Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: Department of Microbiology, The University of Sydney, Sydney, New South Wales 2006, Australia
Methods: DNA sequencing
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5. Compound ID: 1169
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a-Tyvp-(1-3)-+
|
-2)-b-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_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
The structure is contained in the following publication(s):
- 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: 9079895Journal NLM ID: 2985120RPublisher: 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
- Article ID: 5094
Li P, Liu Q, Luo H, Liang K, Yi J, Luo Y, Hu Y, Han Y, Kong Q "O-Serotype Conversion in Salmonella Typhimurium Induces Protective Immune Responses against Invasive Non-Typhoidal Salmonella Infections" -
Frontiers in Immunology 8 (2017) 1647
Salmonella infections remain a big problem worldwide, causing enteric fever by Salmonella Typhi (or Paratyphi) or self-limiting gastroenteritis by non-typhoidal Salmonella (NTS) in healthy individuals. NTS may become invasive and cause septicemia in elderly or immuno-compromised individuals, leading to high mortality and morbidity. No vaccines are currently available for preventing NTS infection in human. As these invasive NTS are restricted to several O-antigen serogroups including B1, D1, C1, and C2, O-antigen polysaccharide is believed to be a good target for vaccine development. In this study, a strategy of O-serotype conversion was investigated to develop live attenuated S. Typhimurium vaccines against the major serovars of NTS infections. The immunodominant O4 serotype of S. Typhimurium was converted into O9, O7, and O8 serotypes through unmarked chromosomal deletion-insertion mutations. O-serotype conversion was confirmed by LPS silver staining and western blotting. All O-serotype conversion mutations were successfully introduced into the live attenuated S. Typhimurium vaccine S738 (Δcrp Δcya) to evaluate their immunogenicity in mice model. The vaccine candidates induced high amounts of heterologous O-polysaccharide-specific functional IgG responses. Vaccinated mice survived a challenge of 100 times the 50% lethality dose (LD50) of wild-type S. Typhimurium. Protective efficacy against heterologous virulent Salmonella challenges was highly O-serotype related. Furthermore, broad-spectrum protection against S. Typhimurium, S. Enteritidis, and S. Choleraesuis was observed by co-vaccination of O9 and O7 O-serotype-converted vaccine candidates. This study highlights the strategy of expressing heterologous O-polysaccharides via genetic engineering in developing live attenuated S. Typhimurium vaccines against NTS infections.
O-antigen, cross-protection, S. Choleraesuis, S. Enteritidis, S. Newport, S. Typhimurium, live attenuated Salmonella vaccine
NCBI PubMed ID: 29255460Publication DOI: 10.3389/fimmu.2017.01647Journal NLM ID: 101560960Publisher: Lausanne: Frontiers Research Foundation
Correspondence: kongqiki@163.com
Institutions: Institute of Preventive Veterinary Medicine, College of Veterinary Medicine, Sichuan Agricultural University, Chengdu, China, Center for Infectious Diseases and Vaccinology, The Biodesign Institute, Arizona State University, Tempe, AZ, United States, College of Animal Science and Technology, Southwest University, Chongqing, China, Department of Infectious Diseases and Pathology, University of Florida, Gainesville, FL, United States
Methods: SDS-PAGE, DNA techniques, ELISA, Western blotting, biological assays, serological methods, genetic methods, statistical analysis, motility assays
- 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: 35608633Publication DOI: 10.1021/acs.chemrev.2c00021Journal NLM ID: 2985134RPublisher: 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
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6. Compound ID: 1170
|
a-Tyvp-(1-3)-+ a-D-Glcp-(1-4)-+
| |
-2)-b-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_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
The structure is contained in the following publication(s):
- 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: 9079895Journal NLM ID: 2985120RPublisher: 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
- 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.2016.11.089Journal NLM ID: 8406899Publisher: 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
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7. Compound ID: 1229
Structure type: fragment of a bigger structure
Compound class: O-antigen
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_149558,IEDB_151528,IEDB_156494,IEDB_190606,IEDB_742246,IEDB_918313,IEDB_918314,SB_165,SB_166,SB_187,SB_195,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 381
Skurnik M, Zhang L "Molecular genetics and biochemistry of Yersinia lipopolysaccharide" -
APMIS: Acta Pathologica, Microbiologica, et Immunologica Scandinavica 104(12) (1996) 849-872
Studies on the molecular genetics of bacterial LPS serve at least two main purposes: (i) to help develop an understanding of the biology, biochemistry and genetics of this bacterial surface macromolecule, and (ii) to provide a basis for both vaccine development and virulence experiments. Both of these goals have been the driving force in studies of Yersinia LPS carried out during the last decade. Here we will review the progress made in the molecular genetics and biochemistry of Yersinia LPS. A deep understanding has been achieved with respect to Y. enterocolitica serotype O:3, reaching as far as a detailed analysis of the gene clusters directing the biosynthesis of the outer core oligosaccharide and of the O-ag. The O-ag gene clusters of Y. enterocolitica serotype O:8 and Y. pseudotuberculosis serotypes O:2a and O:5a have also been cloned and partially characterized LPS biosynthesis of these Yersinia species includes examples of the two major variations recognized in the biosynthesis of this macromolecule: (i) homopolymeric or O-antigen polymerase-independent biosynthesis, and (ii) heteropolymeric or O-antigen polymerase-dependent biosynthesis.
Lipopolysaccharide, genetic, gene, genetics, O-antigen, biochemistry, Yersinia, molecular genetics
NCBI PubMed ID: 9048864Publication DOI: 10.1111/j.1699-0463.1996.tb04951.xJournal NLM ID: 8803400Publisher: Copenhagen: Munksgaard
Institutions: Turku Centre for Biotechnology, University of Turku, Finland, department of Medical Microbiology, University of Turku, Turku, Finland
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8. Compound ID: 1234
|
a-Tyvp-(1-6)-+
|
-3)-a-D-Manp-(1-3)-b-D-Manp-(1-2)-a-D-Manp-(1-3)-a-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_130701,IEDB_137473,IEDB_137485,IEDB_1391961,IEDB_139421,IEDB_140116,IEDB_141584,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_164479,IEDB_885822,IEDB_983930,SB_197,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 381
Skurnik M, Zhang L "Molecular genetics and biochemistry of Yersinia lipopolysaccharide" -
APMIS: Acta Pathologica, Microbiologica, et Immunologica Scandinavica 104(12) (1996) 849-872
Studies on the molecular genetics of bacterial LPS serve at least two main purposes: (i) to help develop an understanding of the biology, biochemistry and genetics of this bacterial surface macromolecule, and (ii) to provide a basis for both vaccine development and virulence experiments. Both of these goals have been the driving force in studies of Yersinia LPS carried out during the last decade. Here we will review the progress made in the molecular genetics and biochemistry of Yersinia LPS. A deep understanding has been achieved with respect to Y. enterocolitica serotype O:3, reaching as far as a detailed analysis of the gene clusters directing the biosynthesis of the outer core oligosaccharide and of the O-ag. The O-ag gene clusters of Y. enterocolitica serotype O:8 and Y. pseudotuberculosis serotypes O:2a and O:5a have also been cloned and partially characterized LPS biosynthesis of these Yersinia species includes examples of the two major variations recognized in the biosynthesis of this macromolecule: (i) homopolymeric or O-antigen polymerase-independent biosynthesis, and (ii) heteropolymeric or O-antigen polymerase-dependent biosynthesis.
Lipopolysaccharide, genetic, gene, genetics, O-antigen, biochemistry, Yersinia, molecular genetics
NCBI PubMed ID: 9048864Publication DOI: 10.1111/j.1699-0463.1996.tb04951.xJournal NLM ID: 8803400Publisher: Copenhagen: Munksgaard
Institutions: Turku Centre for Biotechnology, University of Turku, Finland, department of Medical Microbiology, University of Turku, Turku, Finland
- Article ID: 1778
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 1821
Gorshkova RP, Zubkov VA, Isakov VV, Ovodov YS "Studies on the lipopolysaccharide of Yersinia pseudotuberculosis serotype IVA" -
Bioorganicheskaya Khimia = Bioorganic Chemistry [Russian] 9(10) (1983) 1401-1407
The comparative studied on lipopolysaccharides from Yersinia pseudotuberculosis IVA serovar, strains 32 and 31D, have been conducted. The identity of the lipopolysaccharides isolated from these strains has been shown. The structural pattern of the repeating unit of the O-specific side chain of the lipopolysaccharide has been suggested: (Formula: see text)
NCBI PubMed ID: 6207839Journal NLM ID: 7804941Publisher: Moskva: Nauka
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Sciences Center, Academy of Sciences of the USSR, Vladivostok
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9. Compound ID: 3393
|
a-Tyvp-(1-3)-+
|
-6)-b-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1- |
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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
The structure is contained in the following publication(s):
- 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: 9752996Journal NLM ID: 9315554Publisher: 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
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10. Compound ID: 3411
|
a-Tyvp-(1-3)-+ a-D-Glcp-(1-4)-+
| |
-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136791,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_174035,IEDB_190606,IEDB_225177,IEDB_840979,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 1260
Steinbacher S, Baxa U, Miller S, Weintraub A, Seckler R, Huber R "Crystal structure of phage P22 tailspike protein complexed with Salmonella sp O-antigen receptors" -
Proceedings of the National Academy of Sciences of the USA 93(20) (1996) 10584-10588
The O-antigenic repeating units of lipopolysaccharides from Salmonella serogroups A, B, and D1 serve as receptors for the phage P22 tailspike protein, which also has receptor destroying endoglycosidase (endorhamnosidase) activity, integrating the functions of both hemagglutinin and neuraminidase in influenza virus. Crystal structures of the tailspike protein in complex with oligosaccharides, comprising two O-antigenic repeating units from Salmonella typhimurium, Salmonella enteritidis, and Salmonella typhi 253Ty were determined at 1.8 A resolution. The active-site topology with Asp-392, Asp-395, and Glu-359 as catalytic residues was identified. Kinetics of binding and cleavage suggest a role of the receptor destroying endorhamnosidase activity primarily for detachment of newly assembled phages.
structure, O-antigen, Salmonella, crystal structure, endoglycosidase, hemagglutinin, phage, virus
NCBI PubMed ID: 8855221Journal NLM ID: 7505876Publisher: National Academy of Sciences
Institutions: Abteilung Strukturforschung, Max-Planck-Institut fur Biochemie, Martinsried, Germany, Physikalische Biochemie, Universitat Regensburg, Regensburg, Germany, Department of Immunology, Microbiology, Pathology and Infectious Diseases, Division of Clinical Bacteriology, Huddinge University Hospital, Karolinska Institutet, Huddinge, Sweden
Methods: X-ray
- Article ID: 1323
Zegelaar-Jaarsveld K, van der Plas SC, van der Marel GA, van Boom JH "Preparation of disaccharide haptens corresponding to Salmonella serogroups B and D" -
Journal of Carbohydrate Chemistry 15 (1996) 665-689
The properly protected ethyl 1-thio-abequopyranoside 11 and ethyl 1-thio-tyvelopyranoside 26 were prepared by a sequence of reactions, the key steps of which was the regioselective hydride-mediated ring-opening of the cyclic sulfate function in compound 8 and 18. Iodonium ion-assisted glycosylation of allyl mannopyranoside 30 with the individual ethyl 3,6-dideoxy-1-thio-D-hexopyranoside donors 11 and 26 furnished, after deprotection, the respective allyl 3-O-(a-D-abequopyranosyl)-a-D-mannopyranoside 1 and allyl 3-O-(a-D-tyvelopyranosyl)-a-D-mannopyranoside 2.
synthesis, oligosaccharide, polysaccharide, epitope, serogroup, Salmonella, hapten, disaccharide, abequose, tyvelose
Publication DOI: 10.1080/07328309608005684Journal NLM ID: 8218151Publisher: Marcel Dekker
Institutions: Leiden Institute of Chemistry, Gorlaeus Laboratoria, Leiden University, The Netherlands
- Article ID: 1369
Baxa U, Steinbacher S, Miller S, Weintraub A, Huber R, Seckler R "Interactions of phage P22 tails with their cellular receptor, Salmonella O-antigen polysaccharide" -
Biophysical Journal 71 (1996) 2040-2048
Bacteriophage P22 binds to its cell surface receptor, the repetitive O-antigen structure in Salmonella lipopolysaccharide, by its six homotrimeric tailspikes. Receptor binding by soluble tailspikes and the receptor-inactivating endorhamnosidase activity of the tailspike protein were studied using octa- and dodecasaccharides comprising two and three O-antigen repeats of Salmonella enteritidis and Salmonella typhimurium lipopolysaccharides. Wild-type tailspike protein and three mutants (D392N, D395N, and E359Q) with defective endorhamnosidase activity were used. Oligosaccharide binding to all three subunits, measured by a tryptophan fluorescence quench or by fluorescence depolarization of a coumarin label attached to the reducing end of the dodecasaccharide, occurs independently. At 10 degrees C, the binding affinities of all four proteins to oligosaccharides from both bacterial strains are identical within experimental error, and the binding constants for octa- and dodecasaccharides are 1 x 10(6) M(-1) and 2 x 10(6) M(-1), proving that two O-antigen repeats are sufficient for lipopolysaccharide recognition by the tailspike. Equilibration with the oligosaccharides occurs rapidly, but the endorhamnosidase produces only one cleavage every 100 s at 10 degrees C or about 2 min(-1) at the bacterial growth temperature. Thus, movement of virions in the lipopolysaccharide layer before DNA injection may involve the release and rebinding of individual tailspikes rather than hydrolysis of the O-antigen.
polysaccharide, O-antigen, O antigen, Salmonella, interaction, cellular, receptor, phage
NCBI PubMed ID: 8889178Journal NLM ID: 0370626Publisher: Cambridge, MA: Cell Press
Correspondence: robert.seckler@biologie.uniregensburg.de
Institutions: Universitat Regensberg, Phusikalishe Biochemie, Regensberg, Germany
- Article ID: 1485
Steinbacher S, Miller S, Baxa U, Weintraub A, Seckler R "Interaction of Salmonella phage P22 with its O-antigen receptor studied by X-ray crystallography" -
Biological Chemistry 378(3-4) (1997) 337-343
The O-antigenic repeating units of the Salmonella cell surface lipopolysaccharides (serotypes A, B and D1) serve as receptors for phage P22. This initial binding step is mediated by the tailspike protein (TSP), which is present in six copies on the base plate of the phage. In addition to the binding activity, TSP also displays a low endoglycolytic activity, cleaving the α(1,3)-O-glycosidic bond between rhamnose and galactose of the O-antigenic repeats. The crystal structure of TSP in complex with receptor fragments allowed to identify the receptor binding site for the octasaccharide product of the enzymatic action of TSP on delipidated LPS and the active site consisting of Asp392, Asp395 and Glu359. The structure comprises a large right-handed parallel beta-helix of 13 turns. These fold independently in the trimer, whereas the N-terminus forms a cap-like structure and the C-terminal parts of the three polypeptide strands merge to a single common domain. In addition, TSP has served as model system for the folding of large, multisubunit proteins. Its folding pathway is influenced by a large number of point mutations, classified as lethal, temperature sensitive or general suppressor mutations, which influence the partitioning between aggregation and the productive folding pathway.
O-antigen, Salmonella, crystal structure, endoglycosidase, X-ray crystallography, phage mutants, protein folding, receptor binding, β-helix, virus proyein
NCBI PubMed ID: 9165091Journal NLM ID: 9700112Publisher: Berlin: Walter De Gruyter
Institutions: Max-Planck-Institut für Biochemie, Abteilung für Strukturforschung, Martinsried, Germany, Institut für Biophysik und Physikalische Biochemie, Universitat Regensburg, D-93040 Regensburg, Germany, Department of Immunology, Pathology and Infectious Diseases Division of Clinical Bacteriology, Huddinge University Hospital, Karolinska Institutet, Huddinge, Sweden
Methods: X-ray
- Article ID: 1674
Whitfield C, Valvano MA "Biosynthesis and expression of cell-surface polysaccharides in gram-negative bacteria" -
Advances in Microbial Physiology 35 (1993) 135-246
This chapter provides an overview of the molecular mechanisms involved in synthesis and expression of cell-surface polysaccharides in Gram-negative bacteria. Biosynthesis of many cell-surface components, including polysaccharides, involves enzymes and enzyme complexes found in the cytoplasmic membrane. The peptidoglycan layer is located immediately external to the cytoplasmic membrane and this layer is required for cell shape and rigidity. Gram-negative bacteria possess a periplasm that contains a variety of proteins and enzymes, including some involved in import and export of macromolecules. Biosynthesis of bacterial cell-surface polysaccharides involves a series of sequential processes: (1) biosynthesis of activated precursors in the cytoplasm, (2) formation of repeating units, (3) polymerization of repeating units, and (d) export of polysaccharides to the cell surface. The assembly of polysaccharide repeating units and subsequent polymerization reactions occur at the cytoplasmic membrane, using precursors synthesized in the cytoplasm. Genes for biosynthesis of cell-surface polysaccharides are chromosomal and are arranged in clusters of one or more transcriptional units. The synthesis of lipopolysaccharide (LPS) may be subject to complex regulation, but on-off switching is not possible due to the essential structural requirement for the lipid A-core LPS molecule. Most bacteria use extracellular polysaccharides (EPSs) for protection, and many regulatory strategies are directed to modulating EPS synthesis in response to appropriate environmental cues. Application of genetic and biochemical approaches has facilitated detailed analysis of complex, multicomponent systems, such as those involved in synthesis of cell-surface polysaccharides.
NCBI PubMed ID: 8310880Publication DOI: 10.1016/S0065-2911(08)60099-5Journal NLM ID: 0117147Institutions: Department of Microbiology, University of Guelph, Ontario, Canada, Department of Microbiology, University of Guelph, Guelph, Ontario, Canada, Department of Microbiology and Immunology, University of Western Ontario, London, Ontario, Canada, N6A 5C1
- Article ID: 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?BUS2-0016-0014Publisher: Polish Chemical Society
Correspondence: jerzyg@chemik.chem.univ.gda.pl
Institutions: Wydzial Chemii, Uniwersytet Gdanski, ul. Sobieskiego 18, 80-952 Gdansk
- 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: 25987464Publication DOI: 10.1099/mic.0.000113Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: peter.reeves@sydney.edu.au
Institutions: Department of Microbiology, University of Illinois, Urbana, IL 61801, USA, University of Illinois at Urbana-Champaign, School of Molecular Bioscience, Building D17, University of Sydney, NSW 2006, Australia
Methods: PCR, SDS-PAGE, DNA techniques, genetic methods
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11. Compound ID: 3576
|
a-Tyvp-(1-3)-+ a-D-Glcp-(1-6)-+
| |
-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136105,IEDB_136779,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_174035,IEDB_190606,IEDB_225177,IEDB_840979,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 1323
Zegelaar-Jaarsveld K, van der Plas SC, van der Marel GA, van Boom JH "Preparation of disaccharide haptens corresponding to Salmonella serogroups B and D" -
Journal of Carbohydrate Chemistry 15 (1996) 665-689
The properly protected ethyl 1-thio-abequopyranoside 11 and ethyl 1-thio-tyvelopyranoside 26 were prepared by a sequence of reactions, the key steps of which was the regioselective hydride-mediated ring-opening of the cyclic sulfate function in compound 8 and 18. Iodonium ion-assisted glycosylation of allyl mannopyranoside 30 with the individual ethyl 3,6-dideoxy-1-thio-D-hexopyranoside donors 11 and 26 furnished, after deprotection, the respective allyl 3-O-(a-D-abequopyranosyl)-a-D-mannopyranoside 1 and allyl 3-O-(a-D-tyvelopyranosyl)-a-D-mannopyranoside 2.
synthesis, oligosaccharide, polysaccharide, epitope, serogroup, Salmonella, hapten, disaccharide, abequose, tyvelose
Publication DOI: 10.1080/07328309608005684Journal NLM ID: 8218151Publisher: Marcel Dekker
Institutions: Leiden Institute of Chemistry, Gorlaeus Laboratoria, Leiden University, The Netherlands
- Article ID: 1674
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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12. Compound ID: 3587
Structure type: oligomer
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_139421,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 1323
Zegelaar-Jaarsveld K, van der Plas SC, van der Marel GA, van Boom JH "Preparation of disaccharide haptens corresponding to Salmonella serogroups B and D" -
Journal of Carbohydrate Chemistry 15 (1996) 665-689
The properly protected ethyl 1-thio-abequopyranoside 11 and ethyl 1-thio-tyvelopyranoside 26 were prepared by a sequence of reactions, the key steps of which was the regioselective hydride-mediated ring-opening of the cyclic sulfate function in compound 8 and 18. Iodonium ion-assisted glycosylation of allyl mannopyranoside 30 with the individual ethyl 3,6-dideoxy-1-thio-D-hexopyranoside donors 11 and 26 furnished, after deprotection, the respective allyl 3-O-(a-D-abequopyranosyl)-a-D-mannopyranoside 1 and allyl 3-O-(a-D-tyvelopyranosyl)-a-D-mannopyranoside 2.
synthesis, oligosaccharide, polysaccharide, epitope, serogroup, Salmonella, hapten, disaccharide, abequose, tyvelose
Publication DOI: 10.1080/07328309608005684Journal NLM ID: 8218151Publisher: Marcel Dekker
Institutions: Leiden Institute of Chemistry, Gorlaeus Laboratoria, Leiden University, The Netherlands
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13. Compound ID: 3722
|
a-Tyvp-(1-3)-+
|
-6)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130660,IEDB_130701,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_174033,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 1408
Curd H, Liu D, Reeves PR "Relationships among the O-antigen gene clusters of Salmonella enterica groups B, D1, D2, and D3" -
Journal of Bacteriology 180(4) (1998) 1002-1007
The O antigen is an important cell wall antigen of gram-negative bacteria, and the genes responsible for its biosynthesis are located in a gene cluster. We have cloned and sequenced the DNA segment unique to the O-antigen gene cluster of Salmonella enterica group D3. This segment includes a novel O-antigen polymerase gene (wzyD3). The polymerase gives α(1→6) linkages but has no detectable sequence similarity to that of group D2, which confers the same linkage. We find the remnant of a D3-like wzy gene in the O-antigen gene clusters of groups D1 and B and suggest that this is the original wzy gene of these O-antigen gene clusters.
gene, O-antigen, O antigen, group, cluster, gene cluster, Salmonella, Salmonella enterica, relationship
NCBI PubMed ID: 9473060Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: reeves@angis.usyd.edu.au
Institutions: Department of Microbiology, The University of Sydney,Australia
- Article ID: 1778
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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14. Compound ID: 4214
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Tyvp-(1-2)-+
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-3)-L-Rhap-(1-3)-D-Galp-(1-3)-D-Galp6Ac-(1-
Tyv = 3,6-dideoxy-D-arabino-hexose (tyvelose) |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_136044,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_139421,IEDB_141794,IEDB_149558,IEDB_151528,IEDB_190606,IEDB_225177,IEDB_742246,IEDB_885823,IEDB_918313,IEDB_918314,SB_165,SB_166,SB_187,SB_195,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1568
Szafranek J, Czerwicka M, Kumirska J, Paszkiewicz M, Lojkowska E "Repeating unit structure of Enterobacter sakazakii ZORB A 741 O-polysaccharide" -
Polish Journal of Chemistry 79 (2005)
structure, repeating unit, O-polysaccharide, O polysaccharide, tyvelose, Enterobacter
Journal NLM ID: 7901356Publisher: Państwowe Wydawnictwo Naukowe
Methods: methylation, NMR, sugar analysis
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15. Compound ID: 4441
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a-Tyvp-(1-3)-+ a-D-Glcp2Ac-(1-3)-+
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-4)-b-D-Rhap-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-3)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_130701,IEDB_136044,IEDB_136104,IEDB_137472,IEDB_1394181,IEDB_139421,IEDB_141794,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_190606,IEDB_983930,IEDB_983931,SB_136,SB_165,SB_166,SB_187,SB_192,SB_195,SB_196,SB_44,SB_61,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 1674
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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