Found 57 structures.
Displayed structures from 1 to 15
Next 15 structure(s)
Expand all compounds
Collapse all compounds
Show all as text (SweetDB notation)
Show all graphically (SNFG notation)
1. Compound ID: 129
Structure type: polymer chemical repeating unit
Trivial name: ECA, ECA LPS, enterobacterial common antigen (ECA)
Compound class: enterobacterial common antigen
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 25
Bruix M, Jiménez-Barbero J, Cronet P "Determination by NMR spectroscopy of the structure and conformational features of the enterobacterial common antigen isolated from Escherichia coli" -
Carbohydrate Research 273(2) (1995) 157-170
Complete 1H and 13C spectrum of a polysaccharide isolated from Escherichia coli, which is the major component of the enterobacterial common antigen, has been analyzed through two-dimensional nuclear magnetic resonance spectroscopy. In addition, distance constraints from NOESY and ROESY experiments have been combined with molecular dynamic simulations to determine its major conformation in water solution. Data resulting from both free dynamic simulations and restrained dynamic simulations have been compared with experimental data and discussed
sugar conformation, enterobacterial common antigen, ECA, ECA structure, NMR of ECA
NCBI PubMed ID: 8565004Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Instituto de Estructura de la Materia, C.S.I.C., Madrid, Spain, Instituto de Qulmica Orgdmica, C.S.I.C., Madrid, Spain, European Molecular Biology Laboratory, Heidelberg, Germany
Methods: 13C NMR, 1H NMR, conformation analysis
- Article ID: 1126
Rahman A, Barr K, Rick PD "Identification of the structural gene for the TDP-Fuc4NAc:lipid II Fuc4NAc transferase involved in synthesis of enterobacterial common antigen in Escherichia coli K-12" -
Journal of Bacteriology 183(22) (2001) 6509-6516
The polysaccharide chains of enterobacterial common antigen (ECA) are comprised of the trisaccharide repeat unit Fuc4NAc-ManNAcA-GlcNAc, where Fuc4NAc is 4-acetamido-4,6-dideoxy-D-galactose, ManNAcA is N- acetyl-D-mannosaminuronic acid, and GlcNAc is N-acetyl-D-glucosamine. Individual trisaccharide repeat units are assembled as undecaprenyl- linked intermediates in a sequence of reactions that culminate in the transfer of Fuc4NAc from TDP-Fuc4NAc to ManNAcA-GlcNAc- pyrophosphorylundecaprenol (lipid II) to yield Fuc4NAc-ManNAcA-GlcNAc- pyrophosphorylundecaprenol (lipid III), the donor of trisaccharide repeat units for ECA polysaccharide chain elongation. Most of the genes known to be involved in ECA assembly are located in the wec gene cluster located at ca. 85.4 min on the Escherichia coli chromosome. The available data suggest that the structural gene for the TDP- Fuc4NAc:lipid II Fuc4NAc transferase also resides in the wec gene cluster; however, the location of this gene has not been unequivocally defined. Previous characterization of the nucleotide sequence of the wec gene cluster in the region between o416 and wecG revealed that it contained three open reading frames: o74, o204, and o450. In contrast, the results of experiments described in the current investigation revealed that it contains only two open reading frames, o359 and o450. Mutants of E. coli possessing null mutations in o359 were unable to synthesize ECA, and they accumulated lipid II. In addition, the in vitro incorporation of [(3)H]FucNAc from TDP-[(3)H]Fuc4NAc into lipid II was not observed in reaction mixtures using cell extracts obtained from these mutants as a source of enzyme. The ECA-negative phenotype of these mutants was complemented by plasmid constructs containing the wild-type o359 allele, and Fuc4NAc transferase activity was demonstrated by using cell extracts obtained from the complemented mutants. Furthermore, partially purified o359 gene product, expressed as recombinant C-terminal His-tagged protein, was able to catalyze the in vitro transfer of [(3)H]Fuc4NAc from TDP-[(3)H]Fuc4NAc to lipid II. Our data support the conclusion that o359 of the wec gene cluster of E. coli is the structural gene for the TDP-Fuc4NAc:lipid II Fuc4NAc transferase involved in the synthesis ECA trisaccharide repeat units
biosynthesis, synthesis, transfer, antigen, common, intermediate, blotting, gene, Bacterial, genetics, microbiology, phenotype, structural, Support, characterization, polysaccharide, trisaccharide, cell, chain, linked, Escherichia, Escherichia coli, acid, transferase, lipid, immunology, Molecular Sequence Data, protein, wild type, enterobacterial common antigen, ECA, cluster, gene cluster, Genes, mutant, mutants, common antigen, enterobacterial, activity, assembly, chemical, identification, polysaccharides, region, Open Reading Frames, plasmid, sequence, defined, enzyme, mutation, purified, Western, location, reaction, recombinant, incorporation, U.S.Gov't, source, models, enzymology, chromosome, in vitro, mixture, P.H.S., elongation, extract, Fucosyltransferases
NCBI PubMed ID: 11673418Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: rickp@usuhs.mil
Institutions: Department of Microbiology, Uniformed Services University of Health Sciences, Bethesda, MD 20814-4799, USA
- Article ID: 1142
Rick PD, Barr K, Sankaran K, Kajimura J, Rush JS, Waechter CJ "Evidence that the wzxE gene of Escherichia coli K-12 encodes a protein involved in the transbilayer movement of a trisaccharide-lipid intermediate in the assembly of enterobacterial common antigen" -
Journal of Biological Chemistry 278(19) (2003) 16534-16542
The assembly of many bacterial cell surface polysaccharides requires the transbilayer movement of polyisoprenoid-linked saccharide intermediates across the cytoplasmic membrane. It is generally believed that transverse diffusion of glycolipid intermediates is mediated by integral membrane proteins called translocases or 'flippases.' The bacterial genes proposed to encode these translocases have been collectively designated wzx genes. The wzxE gene of Escherichia coli K- 12 has been implicated in the transbilayer movement of Fuc4NAc-ManNAcA- GlcNAc-P-P-undecaprenol (lipid III), the donor of the trisaccharide repeat unit in the biosynthesis of enterobacterial common antigen (ECA). Previous studies (Feldman, M. F., Marolda, C. L., Monteiro, M. A., Perry, M. B., Parodi, A. J., and Valvano, M. (1999) J. Biol. Chem. 274, 35129-35138) provided indirect evidence that the wzx(016) gene product of E. coli K-12 encoded a translocase capable of mediating the transbilayer movement of N-acetylglucosaminylpyrophosphorylundecaprenol (GlcNAc-P-P-Und), an early intermediate in the synthesis of ECA and many lipopolysaccharide O antigens. Therefore, genetic and biochemical studies were conducted to determine if the putative Wzx(O16) translocase was capable of mediating the transport of N- acetylglucosaminylpyrophosphorylnerol (GlcNAc-P-P-Ner), a water-soluble analogue of GlcNAc-P-P-Und. [(3)H]GlcNAc-P-P-Ner was transported into sealed, everted cytoplasmic membrane vesicles of E. coli K-12 as well as a deletion mutant lacking both the wzx(016) and wzxC genes. In contrast, [(3)H]GlcNAc-P-P-Ner was not transported into membrane vesicles prepared from a wzxE-null mutant, and metabolic radiolabeling experiments revealed the accumulation of lipid III in this mutant. The WzxE transport system exhibited substrate specificity by recognizing both a pyrophosphoryl-linked saccharide and an unsaturated alpha-isoprene unit in the carrier lipid. These results support the conclusion that the wzxE gene encodes a membrane protein involved in the transbilayer movement of lipid III in E. coli
Escherichia coli, enterobacterial common antigen, ECA, A-protein, transport
NCBI PubMed ID: 12621029Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: rickp@usuhs.mil
Institutions: Department of Biochemistry and Molecular Biology, Uniformed Services University of the Health Sciences, Bethesda, Maryland 20814-4799, USA
- Article ID: 1395
Burrows LL, Pigeon KE, Lam JS "Psudomonas aeruginosa B-band lipopolysaccharide genes wbpA and wbpI and their Escherichia coli homologues wecC and wecB are not functionally interchangeable" -
FEMS Microbiology Reviews 189 (2000) 135-141
The O antigen unit of Pseudomonas aeruginosa serotype O5 is a complex trisaccharide containing 2-acetamido-3-acetiminido-2,3-dideoxy- L-D-mannuronic acid, 2-acetimido-3-acetimido-2,3-dideoxy-L-D-mannuronic acid, and 2-acetimido-2,6-deoxy-L-D-galactosamine. Specific knockout mutations in the putative UDP-D-N-acetylglucosamine (UDP-D-GlcNAc) epimerase gene, wbpI, or the putative UDP-D-Nacetylmannosamine dehydrogenase gene, wbpA, resulted in strains that no longer produced B-band lipopolysaccharide, confirming the essential roles of these genes in B-band O antigen synthesis. Despite approximately 50% similarity of wbpI and wbpA to the Escherichia coli genes wecB (rffE) and wecC (rffD) involved in enterobacterial common antigen synthesis, cross-complementation experiments were not successful. These results imply that the P. aeruginosa UDP-D-GlcNAc precursor may be di-N-acetylated prior to further modification, preventing the E. coli enzymes from recognizing it as a substrate.
Lipopolysaccharide, gene, B-band, Escherichia, Escherichia coli, WbpA, WbpI
NCBI PubMed ID: 10930727Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: jlam@uoguelph.ca
Institutions: Department of Microbiology, University of Guelph, Gueph, Canada
Methods: genetic methods
- Article ID: 2400
Basu S, Kuhn HM, Neszm‚lyi A, Himmelspach K, Mayer H "Chemical characterization of enterobacterial common antigen isolated from Plesiomonas shigelloides ATCC 14029" -
European Journal of Biochemistry 162 (1987) 75-81
Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
- Article ID: 3234
Hung MN, Rangarajan E, Munger C, Nadeau G, Sulea T, Matte A "Crystal Structure of TDP-Fucosamine Acetyltransferase (WecD) from Escherichia coli, an Enzyme Required for Enterobacterial Common Antigen Synthesis" -
Journal of Bacteriology 188(15) (2006) 5606-5617
Enterobacterial common antigen (ECA) is a polysaccharide found on the outer membrane of virtually all gram-negative enteric bacteria and consists of three sugars, N-acetyl-d-glucosamine, N-acetyl-d-mannosaminuronic acid, and 4-acetamido-4,6-dideoxy-d-galactose, organized into trisaccharide repeating units having the sequence →3)-α-D-Fuc4NAc-(1→4)-β-D-ManNAcA-(1→4)-α-D-GlcNAc-(1→. While the precise function of ECA is unknown, it has been linked to the resistance of Shiga-toxin-producing Escherichia coli (STEC) O157:H7 to organic acids and the resistance of Salmonella enterica to bile salts. The final step in the synthesis of 4-acetamido-4,6-dideoxy-d-galactose, the acetyl-coenzyme A (CoA)-dependent acetylation of the 4-amino group, is carried out by TDP-fucosamine acetyltransferase (WecD). We have determined the crystal structure of WecD in apo form at a 1.95-A resolution and bound to acetyl-CoA at a 1.66-A resolution. WecD is a dimeric enzyme, with each monomer adopting the GNAT N-acetyltransferase fold, common to a number of enzymes involved in acetylation of histones, aminoglycoside antibiotics, serotonin, and sugars. The crystal structure of WecD, however, represents the first structure of a GNAT family member that acts on nucleotide sugars. Based on this cocrystal structure, we have used flexible docking to generate a WecD-bound model of the acetyl-CoA-TDP-fucosamine tetrahedral intermediate, representing the structure during acetyl transfer. Our structural data show that WecD does not possess a residue that directly functions as a catalytic base, although Tyr208 is well positioned to function as a general acid by protonating the thiolate anion of coenzyme A.
synthesis, Escherichia coli, enterobacterial common antigen, ECA, crystal structure
NCBI PubMed ID: 16855251Publication DOI: 10.1128/JB.00306-06Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: allan.matte@nrc-cnrc.gc.ca
Institutions: Biotechnology Research Institute, National Research Council of Canada, 6100 Royalmount Avenue, Montreal, Quebec H4P 2R2, Canada, Department of Biochemistry, McGill University, Montreal, Quebec Canada
Methods: crystallization, two-wavelength MAD experiment
- Article ID: 3685
Duda KA, Duda KT, Beczala A, Kasperkiewicz K, Radziejewska-Lebrecht J, Skurnik M "ECA-immunogenicity of Proteus mirabilis strains" -
Archivum Immunologiae et Therapiae Experimentalis 57(2) (2009) 147-151
INTRODUCTION: Bacteria of the genus Proteus are opportunistic pathogens and cause mainly urinary tract infections. They also play a role in the pathogenesis of reactive arthritis (RA). Patients suffering from Yersinia-triggered RA often carry high titers of antibodies specific to enterobacterial common antigen (ECA). The immunogenicity of ECA has not received much attention thus far and studies have focused mainly on the ECA of Escherichia coli and Yersinia enterocolitica. In this paper the ECA-immunogenicity of Proteus mirabilis is elucidated using two wild-type strains (S1959 and O28) as well as their rough (R) derivative strains R110/1959, which expresses lipopolysaccharide (LPS) with a full core, and R4/O28, which expresses LPS with only an inner core. MATERIALS AND METHODS: Rabbit polyclonal antisera were produced by immunization with boiled suspensions of the four P. mirabilis strains. The antisera were tested for the presence of antibodies specific to ECA by Western blotting using glycerophospholipid-linked ECA (ECA( PG )) of Salmonella montevideo as antigen. Lipopolysaccharide (LPS) was isolated from the four strains by the hot phenol/water procedure in which ECA( PG ) is co-extracted with LPS and by the phenol/chloroform/petroleum ether extraction that results in the isolation of LPS and/or LPS-linked ECA (ECA( LPS )) free of ECA( PG ). The LPS preparations were tested for the presence of ECA by Western blotting using ECA-specific antibodies. RESULTS: The results demonstrated that all four P. mirabilis strains were ECA immunogenic. The rabbit antisera immunized by the four strains all contained ECA-specific antibodies. Analysis of the LPS preparations demonstrated that the P. mirabilis wild-type strains O28 and S1959 and the Ra mutant strain R110/1959 expressed ECA( LPS ), suggesting that it induced the anti-ECA antibody responses. Only the presence of ECA( PG ) could be demonstrated in the Rc mutant strain R4/O28. CONCLUSIONS: These results therefore suggest that, similar to E. coli, LPS with a full core is also required as the acceptor of ECA for P. mirabilis strains to produce ECA( LPS ). Since ECA( PG ) is not immunogenic unless combined with some proteins, it is likely that ECA( PG )-protein complexes formed during the intravenous immunization with the Rc mutant strain R4/O28
Lipopolysaccharide, enterobacterial common antigen, Proteus mirabilis, S and R strains, ECA immunogenicity
NCBI PubMed ID: 19333729Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: mikael.skurnik@helsenki.fi
Institutions: Department of Microbiology, Faculty of Biology and Environment Protection, University of Silesia, Katowice, Poland
Methods: SDS-PAGE, Western blotting, serological methods
- Article ID: 4524
Gozdziewicz TK, Lugowski C, Lukasiewicz J "First evidence for a covalent linkage between enterobacterial common antigen and lipopolysaccharide in Shigella sonnei phase II ECALPS" -
Journal of Biological Chemistry 289(5) (2014) 2745-2754
Enterobacterial common antigen (ECA) is expressed by Gram-negative bacteria belonging to Enterobacteriaceae, including emerging drug-resistant pathogens such as Escherichia coli, Klebsiella pneumoniae, and Proteus spp. Recent studies have indicated the importance of ECA for cell envelope integrity, flagellum expression, and resistance of enteric bacteria to acetic acid and bile salts. ECA, a heteropolysaccharide built from the trisaccharide repeating unit, →3)-α-D-Fucp4NAc-(1→4)-β-D-ManpNAcA-(1→4)-α-D-GlcpNAc-(1→, occurs as a cyclic form (ECACYC), a phosphatidylglycerol (PG)-linked form (ECAPG), and an endotoxin/lipopolysaccharide (LPS)-associated form (ECALPS). Since the discovery of ECA in 1962, the structures of ECAPG and ECACYC have been completely elucidated. However, no direct evidence has been presented to support a covalent linkage between ECA and LPS; only serological indications of co-association have been reported. This is paradoxical, given that ECA was first identified based on the capacity of immunogenic ECALPS to elicit antibodies cross-reactive with enterobacteria. Using a simple isolation protocol supported by serological tracking of ECA epitopes and NMR spectroscopy and mass spectrometry, we have succeeded in the first detection, isolation, and complete structural analysis of poly- and oligosaccharides of Shigella sonnei phase II ECALPS. ECALPS consists of the core oligosaccharide substituted with one to four repeating units of ECA at the position occupied by the O-antigen in the case of smooth S. sonnei phase I. These data represent the first structural evidence for the existence of ECALPS in the half-century since it was first discovered and provide insights that could prove helpful in further structural analyses and screening of ECALPS among Enterobacteriaceae species.
Escherichia coli, enterobacterial common antigen, ECA, Shigella sonnei, Klebsiella pneumoniae, cell envelope, flagella, mass spectrometry (MS), hase II
NCBI PubMed ID: 24324266Publication DOI: 10.1074/jbc.M113.512749Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: czaja@iitd.pan.wroc.pl
Institutions: Department of Immunochemistry, Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, SDS-PAGE, 31P NMR, ESI-MS, mild acid hydrolysis, composition analysis, NMR-1D, serological methods, immunoblotting
- Article ID: 4583
Muszynski A, Rabsztyn K, Knapska K, Duda KA, Duda-Grychtol KT, Kasperkiewicz K, Radziejewska-Lebrecht J, Holst O, Skurnik M "Enterobacterial common antigen and O-specific polysaccharide coexist in the lipopolysaccharide of Yersinia enterocolitica serotype O:3" -
Microbiology 159(Pt8) (2013) 1782-1793
Yersinia enterocolitica serotype O:3 produces two types of lipopolysaccharide (LPS) molecules to its surface. In both types the lipid A (LA) structure is substituted by inner core (IC) octasaccharide to which either outer core (OC) hexasaccharide or homopolymeric O-polysaccharide (OPS) is linked. In addition, enterobacterial common antigen (ECA) can be covalently linked to LPS, however, via an unknown linkage. To elucidate the relationship between ECA and LPS in Y. enterocolitica O:3 and the effect of temperature on their expression, LPS was isolated from bacteria grown at 22 degrees C and 37 degrees C by consequent hot phenol/water (PhW) and phenol-chloroform-light petroleum (PCP) extractions to obtain LPS preparations free of ECA linked to glycerophospholipid. In immunoblotting, monoclonal antibodies TomA6 and 898, specific for OPS and ECA, respectively, reacted both with ladder-like bands and a slower-migrating smear suggesting that the ECA and OPS epitopes co-exist on same molecules. These results were supported by immunoblotting with a monovalent Y. enterocolitica O:3 ECA-specific rabbit antiserum. Also, two or three 898-positive (and monovalent-positive) TomA6-negative bands migrated at the level of the LA-IC band in LPS samples from certain OC mutants; most likely representing LA-IC molecules carrying 1-3 ECA repeat units but no OPS. These bands were also present in Y. enterocolitica O:9 OC mutants, however, co-existence of ECA and OPS in same molecules could not be detected. Finally, the LA-IC-ECA bands were missing from LPS of bacteria grown at 37 degrees C and also the general reduction in wild type bacteria of ECA-specific monovalent-reactive material at 37 degrees C suggested that temperature regulates the expression of ECA. Indeed, RNA-sequencing analysis showed significant downregulation of the ECA biosynthetic gene cluster at 37 degrees C.
Lipopolysaccharide, monoclonal antibodies, epitopes, enterobacterial common antigen, gene cluster, O-specific polysaccharide, Yersinia enterocolitica
NCBI PubMed ID: 23782803Publication DOI: 10.1099/mic.0.066662-0Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: Mikael Skurnik
Institutions: Department of Microbiology, University of Silesia, Katowice, Poland, Department of Bacteriology and Immunology, Haartman Institute, Research Programs Unit, Immunobiology, University of Helsinki, Helsinki, Finland, Division of Structural Biochemistry, Research Center Borstel, Leibniz-Center for Medicine and Biosciences, Airway Research Center North (ARCN), Member of the German Center for Lung Research (DZL), Borstel, Germany, Helsinki University Central Hospital Laboratory Diagnostics, Helsinki, Finland
Methods: sugar analysis, DOC-PAGE, serological methods, genetic methods, immunoblotting
- Article ID: 4779
Ogrodzki P, Forsythe S "Capsular profiling of the Cronobacter genus and the association of specific Cronobacter sakazakii and C. malonaticus capsule types with neonatal meningitis and necrotizing enterocolitis" -
BMC Genomics 16(1) (2015) 758
BACKGROUND: Cronobacter sakazakii and C. malonaticus can cause serious diseases especially in infants where they are associated with rare but fatal neonatal infections such as meningitis and necrotising enterocolitis.METHODS: This study used 104 whole genome sequenced strains, covering all seven species in the genus, to analyse capsule associated clusters of genes involved in the biosynthesis of the O-antigen, colanic acid, bacterial cellulose, enterobacterial common antigen (ECA), and a previously uncharacterised K-antigen.RESULTS: Phylogeny of the gnd and galF genes flanking the O-antigen region enabled the defining of 38 subgroups which are potential serotypes. Two variants of the colanic acid synthesis gene cluster (CA1 and CA2) were found which differed with the absence of galE in CA2. Cellulose (bcs genes) were present in all species, but were absent in C. sakazakii sequence type (ST) 13 and clonal complex (CC) 100 strains. The ECA locus was found in all strains. The K-antigen capsular polysaccharide Region 1 (kpsEDCS) and Region 3 (kpsMT) genes were found in all Cronobacter strains. The highly variable Region 2 genes were assigned to 2 homology groups (K1 and K2). C. sakazakii and C. malonaticus isolates with capsular type [K2:CA2:Cell(+)] were associated with neonatal meningitis and necrotizing enterocolitis. Other capsular types were less associated with clinical infections.CONCLUSION: This study proposes a new capsular typing scheme which identifies a possible important virulence trait associated with severe neonatal infections. The various capsular polysaccharide structures warrant further investigation as they could be relevant to macrophage survival, desiccation resistance, environmental survival, and biofilm formation in the hospital environment, including neonatal enteral feeding tubes.
Cronobacter sakazakii, Cronobacter, capsula formation, genomic analysis
NCBI PubMed ID: 26449318Publication DOI: 10.1186/s12864-015-1960-zJournal NLM ID: 100965258Publisher: London: BioMed Central
Correspondence: Stephen.forsythe@ntu.ac.uk
Institutions: Pathogen Research Group, School of Science and Technology, Nottingham Trent University, Clifton Lane, NG11 8NS, Nottingham, UK
Methods: genetic methods, bioinformatic analysis, phylogenetic analysis
- Article ID: 4846
Gozdziewicz TK, Łukasiewicz J, Ługowski C "The structure and significance of enterobacterial common antigen (ECA)" -
Postȩpy Higieny i Medycyny Doświadczalnej [Polish] 69 (2015) 1003-1012
The enterobacterial common antigen (ECA) is a carbohydrate-derived cell surface antigen present in all Gram-negative bacteria belonging to Enterobacteriaceae family. Biosynthetic pathways shared by ECA and LPS (endotoxin) suggest close connections between these antigens. ECA occurs in three different forms: a phosphatidyl-linked linear polysaccharide anchored on the cell surface (ECAPG), a cyclic form built of 4-6 repeating units localized in the periplasm (ECACYC) and as a linear polysaccharide covalently linked to LPS core oligosaccharide (ECALPS). Regardless of ECA form, poly- and oligosaccharides of ECA consist of the biological trisaccharide repeating units: →3)-α-d-Fucp4NAc-(1→4)-β-d-ManpNAcA-(1→4)-α-d-GlcpNAc-(1→, where Fucp4NAc refers to 4-acetamido-2,4-dideoxygalactose, ManpNAcA to N-acetyl-mannosaminuronic acid and GlcpNAc to N-acetylglucosamine. ECAPG and ECALPS consisting of one unit with Fucp4NAc as a terminal sugar were also identified. The number of the studies shows its occurrence in all members of enteric bacteria with a few exceptions such as Erwinia chrysanthemi. The presence of ECA was also shown for such genera as Plesiomonas [4] and Yersinia [36], previously belonging to the Vibrionaceae and Pasteurellaceae families, respectively. It was one of the reasons to include these two taxa in the Enterobacteriaceae family. The function of ECA is not fully understood, but it was reported that its occurrence is important in resistance of bacterial cells to environmental conditions, such as bile salts in the human digestive tract. The immunogenicity of ECA seems very interesting in the fact that only sparse rough Gram-negative strains, such as Shigella sonnei phase II, Escherichia coli R1, R2, R4, K-12, and Yersinia enterocolitica O:3 are able to induce the production of specific anti-ECA antibodies. It is the effect of the ECALPS, and the evidence for the existence of such covalent linkage was provided by structural analysis of S. sonnei surface antigens.
LPS, enterobacterial common antigen, ECA, Shigella sonnei, sepsis, lipopolysaccharid
NCBI PubMed ID: 26400887Journal NLM ID: 0421052Publisher: Warszawa: Panstwowy Zaklad Wydawnictw Lekarskich
Correspondence: tomasz.gozdziewicz@iitd.pan.wroc.pl
Institutions: Instytut Immunologii i Terapii Doświadczalnej PAN im. Ludwika Hirszfelda we Wrocławiu, Uniwersytet Opolski
- Article ID: 4860
Noszczyńska M, Kasperkiewicz K, Duda KA, Podhorodecka J, Rabsztyn K, Gwizdala K, Swierzko AS, Radziejewska-Lebrecht J, Holst O, Skurnik M "Serological characterization of the enterobacterial common antigen substitution of the lipopolysaccharide of Yersinia enterocolitica O : 3" -
Microbiology (2015) 219-227
Enterobacterial common antigen (ECA) is a polysaccharide present in all members of Enterobacteriaceae anchored either via phosphatidylglycerol (PG) or LPS to the outer leaflet of the outer membrane (ECAPG and ECALPS, respectively). Only the latter form is ECA-immunogenic. We previously demonstrated that Yersinia enterocolitica O : 3 and its rough (O-specific polysaccharide-negative) mutants were ECA-immunogenic, suggesting that they contained ECALPS; however, it was not known which part of the LPS core region was involved in ECA binding. To address this, we used a set of three deep-rough LPS mutants for rabbit immunization. The polyvalent antisera obtained were: (i) analysed for the presence of anti-LPS and anti-ECA antibodies; (ii) treated with caprylic acid (CA) to precipitate IgM antibodies and protein aggregates; and (iii) adsorbed with live ECA-negative bacteria to obtain specific anti-ECA antisera. We demonstrated the presence of antibodies specific for both ECAPG and ECALPS in all antisera obtained. Both CA treatment and adsorption with ECA-negative bacteria efficiently removed anti-LPS antibodies, resulting in specific anti-ECA sera. The LPS of the ECALPS-positive deepest-rough mutant contained only lipid A and 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) residues of the inner core, suggesting that ECALPS was linked to the Kdo region of LPS in Y. enterocolitica O : 3.
lipopolysaccharides, LPS, lipid A, enterobacterial common antigen, ECA, serological, classification, serotyping, LPS core, Yersinia enterocolitica O3, YeO3 mutants
NCBI PubMed ID: 25406452Publication DOI: 10.1099/mic.0.083493-0Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: mikael.skurnik@helsinki.fi
Institutions: Division of Structural Biochemistry, Research Center Borstel, Leibniz-Center for Medicine and Biosciences, Borstel, Germany, Department of Microbiology, University of Silesia, Jagiellońska 28, PL- 40-032 Katowice, Poland, Department of Immunobiology of Infections, Institute of Medical Biology, PAS, Lodowa 106, PL- 93-232 Lodz, Poland, Department of Bacteriology and Immunology, Haartman Institute, and Research Programs Unit, Immunobiology, University of Helsinki, FIN-00014, Helsinki, Finland, Helsinki University Central Hospital Laboratory Diagnostics, FIN-00270 Helsinki, Finland
Methods: PCR, SDS-PAGE, ELISA, ESI-MS, DOC-PAGE, GC, composition analysis, serological methods, genetic methods
- Article ID: 4946
Merino S, Gonzalez V, Tomas JM "The first sugar of the repeat units is essential for the Wzy polymerase activity and elongation of the O-antigen lipopolysaccharide" -
Future Microbiology 11 (2016) 903-918
In the Wzx/Wzy-dependent assembled pathway, the assembled O-antigen repeat units are translocated from the cytosolic to the periplasmic face of the inner membrane by a Wzx translocase and then, polymerized by the integral membrane protein Wzy to form a glycan chain. We demonstrate that the activity of the Escherichia coli O-antigen polymerase (Wzy) is dependent on the first sugar of the O-antigen repeat unit to produce the O-antigen polymerization and therefore, there is a need for a concerted action with the enzyme transferring the initial HexNAc to undecaprenyl phosphate (UDP-HexNAc: polyprenol-P HexNAc-1-P transferase). Furthermore, in the case of Aeromonas hydrophila Wzy-O34 polymerization activity, the enzyme is permissive with the sugar at the nonreducing end of the O-antigen repeat unit.
Lipopolysaccharide, Escherichia coli, Aeromonas hydrophila, O-antigen polymerization, Wzy O-antigen assembly pathway
NCBI PubMed ID: 27357519Publication DOI: 10.2217/fmb-2015-0028Journal NLM ID: 101278120Publisher: London: Future Medicine
Correspondence: jtomas@ub.edu
Institutions: Departamento de Microbiologia, Facultad de Biologia, Universidad de Barcelona, Diagonal 643, 08071 Barcelona, Spain, Institute of Virology, Hannover Medical School, Hannover, Germany
Methods: PCR, GC-MS, SDS-PAGE, DNA techniques, acid hydrolysis, GLC, genetic methods, computer sequence analysis
- Article ID: 5188
Micoli F, Costantino P, Adamo R "Potential targets for next generation anti-microbial glycoconjugate vaccines" -
FEMS Microbiology Reviews 42(3) (2018) 388-423
Cell surface carbohydrates have been proven optimal targets for vaccine development. Conjugation of polysaccharides to a carrier protein triggers a T-cell dependent immune response to the glycan moiety. Licensed glycoconjugate vaccines are produced by chemical conjugation of capsular polysaccharides to prevent meningitis caused by meningococcus, pneumococcus and Haemophilus influenzae type b. However, other classes of carbohydrates (O-antigens, exopolysaccharides, wall/teichoic acids) represent attractive targets for developing vaccines.Recent analysis from WHO/CHO underpins alarming concern towards antibiotic resistant bacteria, such as the so called ESKAPE pathogens (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa and Enterobacter spp.) and additional pathogens such as Clostridium difficile and Group A Streptococcus. Fungal infections are also becoming increasingly invasive for immunocompromised patients or hospitalized individuals. Other emergencies could derive from bacteria which spread during environmental calamities (Vibrio cholerae) or with potential as bioterrorism weapons (Burkholderia pseudomallei and mallei, Francisella tularensis). Vaccination could aid reducing the use of broad spectrum antibiotics and provide protection by herd immunity also to individuals who are not vaccinated.This review analyses structural and functional differences of the polysaccharides exposed on the surface of emerging pathogenic bacteria, combined with medical need and technological feasibility of corresponding glycoconjugate vaccines.
carbohydrates, glycoconjugates, vaccines, glycoengineering, antimicrobial resistance
NCBI PubMed ID: 29547971Publication DOI: 10.1093/femsre/fuy011Journal NLM ID: 8902526Publisher: Oxford University Press
Correspondence: Roberto Adamo
Institutions: GSK Vaccines Institute for Global Health (GVGH), Via Fiorentina 1, 53100 Siena
- Article ID: 5813
Maciejewska A, Kaszowska M, Jachymek W, Lugowski C, Lukasiewicz J "Lipopolysaccharide-Linked Enterobacterial Common Antigen (ECALPS) Occurs in Rough Strains of Escherichia coli R1, R2, and R4" -
International Journal of Molecular Sciences 21(17) (2020) 6038
Enterobacterial common antigen (ECA) is a conserved surface antigen characteristic for Enterobacteriaceae. It is consisting of trisaccharide repeating unit, →3)-α-d-Fucp4NAc-(1→4)-β-d-ManpNAcA-(1→4)-α-d-GlcpNAc-(1→, where prevailing forms include ECA linked to phosphatidylglycerol (ECAPG) and cyclic ECA (ECACYC). Lipopolysaccharide (LPS)-associated form (ECALPS) has been proved to date only for rough Shigella sonnei phase II. Depending on the structure organization, ECA constitutes surface antigen (ECAPG and ECALPS) or maintains the outer membrane permeability barrier (ECACYC). The existence of LPS was hypothesized in the 1960-80s on the basis of serological observations. Only a few Escherichia coli strains (i.e., R1, R2, R3, R4, and K-12) have led to the generation of anti-ECA antibodies upon immunization, excluding ECAPG as an immunogen and conjecturing ECALPS as the only immunogenic form. Here, we presented a structural survey of ECALPS in E. coli R1, R2, R3, and R4 to correlate previous serological observations with the presence of ECALPS. The low yields of ECALPS were identified in the R1, R2, and R4 strains, where ECA occupied outer core residues of LPS that used to be substituted by O-specific polysaccharide in the case of smooth LPS. Previously published observations and hypotheses regarding the immunogenicity and biosynthesis of ECALPS were discussed and correlated with presented herein structural data.
Lipopolysaccharide, NMR, LPS, enterobacterial common antigen, ECA, endotoxin, mass spectrometry, ECALPS
NCBI PubMed ID: 32839412Publication DOI: 10.3390/ijms21176038Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: jolanta.lukasiewicz@hirszfeld.pl
Institutions: Laboratory of Microbial Immunochemistry and Vaccines, Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, ESI-MS, MS/MS, MALDI-TOF MS
Expand this compound
Collapse this compound
2. Compound ID: 210
|
EtN-(1--P--7)--+
|
a-L-Rhap-(1-4)-a-D-Glcp-(1-2)-L-gro-a-D-manHepp-(1-3)-+ | P-4)-+
| | |
R-3HOBut-(1-4)-a-D-Fucp4N-(1-4)-a-Legp5Ac7Ac-(2-6)-b-D-Glcp-(1-4)-D-gro-a-D-manHepp-(1-5)-Kdo
|
EtN-(1--P--2)--+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_136105,IEDB_137777,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_2189046,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 52
Edebrink P, Jansson P, Bogwald J, Hoffman J "Structural studies of the Vibrio salmonicida lipopolysaccharide" -
Carbohydrate Research 287 (1996) 225-245
The oligosaccharide part of the Vibrio salmonicida (strain NCMB 2262) lipopolysaccharide was isolated by mild acid hydrolysis followed by gel-permeation chromatography. The structure was established mainly by methylation analysis, mass spectrometry, and NMR spectroscopy. It is concluded that the oligosaccharide has the following structure, in which L-α-D-Hepp is L-glycero-α-D-manno-heptopyranose, D-α-D-Hepp is D-glycero-α-D-manno-heptopyranose, α-D-Fucp4N is 4-amino-4,6-dideoxy-α-D-galactopyranose, α-NonA is 5-acetamidino-7-acetamido-3,5,7, 9-tetradeoxy-L-glycero-α-D-galacto-nonulosonic acid, BA is (R)-3-hydroxybutanoyl, and PEA is phosphoethanolamine. The substitution pattern of the branching heptosyl residue was deduced from 1H NMR chemical shifts and conformations of the branching region, obtained by molecular modeling. The absolute configuration for NonA was determined by NMR spectroscopy from NOE correlations to the neighbouring sugar and 13C NMR chemical shift data. It could also be shown that assignments of nonulosonic acids with the D-glycero-L-galacto configuration, reported by previous investigators, are erroneous and should be changed to L-glycero-D-galacto. The oligosaccharide is assumed to be linked to the 5-position of a Kdo residue, phosphorylated in the 4-position as observed for other lipopolysaccharides from Vibrionaceae. [formula: see text]
Lipopolysaccharide, NMR, structure, Salmon, nonulosonic acid
NCBI PubMed ID: 8766209Publication DOI: 10.1016/0008-6215(96)00076-6Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Stockholm University, Sweden, Clinical Research Centre, Analitycal Unit, Karolinska Institute, Huddinge, Sweden, Norwegian Institute of Fisheries and Aquaculture Ltd, Tromso, Norway
Methods: methylation, NMR-2D, NMR, sugar analysis, MS
- Article ID: 5195
Norstebo SF, Lotherington L, Landsverk M, Bjelland AM, Sorum H "Aliivibrio salmonicida requires O-antigen for virulence in Atlantic salmon (Salmo salar L.)" -
Microbial Pathogenesis 124 (2018) 322-331
Aliivibrio salmonicida is the causative agent of cold-water vibriosis, a hemorrhagic septicemia of salmonid fish. The bacterium has been shown to rapidly enter the fish bloodstream, and proliferation in blood is seen after a period of latency. Although the pathogenesis of the disease is largely unknown, shedding of high quantities of outer-membrane complex VS-P1, consisting of LPS and a protein moiety, has been suggested to act as decoy and contribute to immunomodulation. To investigate the role of LPS in the pathogenesis, we constructed O-antigen deficient mutants by knocking out the gene encoding O-antigen ligase waaL. As this gene exists in two copies in the Al. salmonicida genome, we constructed single and double in-frame deletion mutants to explore potential effects of copy number variation. Our results demonstrate that the LPS structure of Al. salmonicida is essential for virulence in Atlantic salmon. As the loss of O-antigen did not influence invasive properties of the bacterium, the role of LPS in virulence applies to later stages of the pathogenesis. One copy of waaL was sufficient for O-antigen ligation and virulence in experimental models. However, as a non-significant decrease in mortality was observed after immersion challenge with a waaL single mutant, it is tempting to suggest that multiple copies of the gene are beneficial to the bacterium at lower challenge doses. The loss of O-antigen was not found to affect serum survival in vitro, but quantification of bacteria in blood following immersion challenge suggested a role in in vivo survival. Furthermore, fish challenged with the waaL double mutant induced a more transient immune response than fish challenged with the wild type strain. Whether the reduction in virulence following the loss of waaL is caused by altered immunomodulative properties or impaired survival remains unclear. However, our data demonstrate that LPS is crucial for development of disease.
Lipopolysaccharide, Pathogenesis, O-antigen, Atlantic salmon, Aliivibrio salmonicida, Cold-water vibriosis
NCBI PubMed ID: 30165113Publication DOI: 10.1016/j.micpath.2018.08.058Journal NLM ID: 8606191Publisher: Academic Press
Correspondence: S.F. Norstebo
Institutions: Department of Food Safety and Infection Biology, Faculty of Veterinary Medicine, Norwegian University of Life Sciences, PO Box 8146 Dep, 0033, Oslo, Norway, Department of Mechanical, Electronic and Chemical Engineering, Oslo and Akershus University College of Applied Sciences, PO Box 4 St. Olavs Plass, 0130, Oslo, Norway
Methods: virulence assays, SDS-PAGE, DNA techniques, cytokine analysis, RT-PCR, RNA extraction
Expand this compound
Collapse this compound
3. Compound ID: 272
| Cyclic
-3)-a-D-Fucp4NAc-(1-4)-b-D-ManpNAcA-(1-4)-a-D-GlcpNAc-(1- |
Show graphically |
Structure type: cyclic polymer repeating unit
; n=4
Trivial name: Enterobacterial common antigen
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 71
Färnbäck M, Eriksson L, Senchenkova SN, Zych K, Knirel YA, Sidorczyk Z, Widmalm G "Crystal structure of a cyclic enterobacterial common antigen" -
Angewandte Chemie, International Edition 42 (2003) 2543-2546
No Abstract
antigen, structure, common, enterobacterial common antigen, common antigen, crystal, crystal structure, cyclic, enterobacterial
NCBI PubMed ID: 12800183Journal NLM ID: 0370543Publisher: Weinheim: Wiley-VCH
Correspondence: gw@organ.su.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden
Methods: X-ray
- Article ID: 384
Staaf M, Hoog C, Stevensson B, Maliniak A, Widmalm G "Conformational investigation of a cyclic enterobacterial common antigen employing NMR spectroscopy and molecular dynamics simulations" -
Biochemistry 40(12) (2001) 3623-3628
The three-dimensional structure of a cyclic enterobacterial common antigen (ECA) having four trisaccharide repeating units has been investigated by NMR spectroscopy and molecular dynamics simulations. Three different NMR parameters were determined: (a) (1)H,(1)H cross-relaxation rates from NOE experiments were used for determination of proton-proton distances; (b) trans-glycosidic (3)J(C,H) scalar coupling constants analyzed via a Karplus-type relationship provided information on torsion angles; and (c) (1)H,(13)C one-bond dipolar couplings obtained in a dilute liquid-crystalline medium were interpreted in terms of the orientational order and molecular conformations. The molecular dynamics simulations of the dodecasaccharide were performed with explicit water and counterions, which are important factors that strongly influence molecular conformation. Subsequently, the results from computer simulation were used to generate a three-dimensional structure of the cyclic ECA which is consistent with the experimental NMR parameters.
conformational, dynamics, molecular dynamics, NMR spectroscopy, enterobacterial common antigen, cyclic, simulation
NCBI PubMed ID: 11297429Journal NLM ID: 0370623Publisher: American Chemical Society
Correspondence: G. Widmalm
Institutions: Department of Organic Chemistry and DiVision of Physical Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
Methods: NMR, MD simulations
- Article ID: 1602
Andersson A, Ahl A, Eklund R, Widmalm G, Maler L "Dynamics in the cyclic enterobacterial common antigen as studied by 13C NMR relaxation" -
Journal of Biomolecular NMR 31(4) (2005) 311-320
The motional properties of the cyclic enterobacterial common antigen (cECA), consisting of four trisaccharide repeat units, have been investigated by carbon-13 spin relaxation. R(1), R(2) and NOE relaxation parameters have been determined at three magnetic field strengths. The data were interpreted within the model-free framework to include the possibility of motional anisotropy, and overall as well as local dynamical parameters were fitted separately for each ring carbon. The motional anisotropy was addressed by assuming an axially symmetric diffusion tensor, which was fitted from the overall correlation times for each site in the sugar residues using the previously determined crystal structure. The data were found to be in agreement with an oblate shape of the molecule, and the values for D(iso) and D(||)/D(perpendicular sign) were in good agreement with translational diffusion data and an estimate based on calculation of the moment of inertia tensor, respectively. The local dynamics in cECA were found to be residue-dependent. Somewhat lower values for the order parameters, as well as longer local correlation times, were observed for the β-linked ManNAcA residue compared to the two α-linked residues in the trisaccharide repeat unit
NMR, antigen, lipopolysaccharides, X-ray, Oligosaccharides, dynamics, enterobacterial common antigen, common antigen, crystal, crystal structure, Magnetic Resonance Spectroscopy, 13C NMR, NOE, models, Molecular Conformation, Plesiomonas, Crystallography, anisotropy, Hexosamines
NCBI PubMed ID: 15928997Journal NLM ID: 9110829Publisher: ESCOM Science Publishers
Correspondence: lena.maler@dbb.su.se
Institutions: Department of Biochemistry and Biophysics, Arrhenius Laboratory, Stockholm University, Sweden
Methods: NMR
Expand this compound
Collapse this compound
4. Compound ID: 823
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_115015,IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142489,IEDB_149135,IEDB_151531,SB_86
The structure is contained in the following publication(s):
- Article ID: 224
Winn AM, Miles CT, Wilkinson SG "Structure of the O3 antigen of Stenotrophomonas (Xanthomonas or Pseudomonas) maltophilia" -
Carbohydrate Research 282 (1996) 149-156
The O atnigen isolated from the lipopolysaccharide of a strain of Stenotrophomonas (Xanthomonas or Pseudomonas) maltophilia serogroup O3 was found to contain 4-acetamido-4,6,-dideoxy-D-galactose, D-fucose, and N-acetyo-D-glucosamine. By means of chemical degradations and NMR spectroscopy the repeating unit of the O-specific polymer was determined to by a branched trisaccharide repeating-unit of the structure shown. [see formula in text]
Lipopolysaccharide, O-antigen, Stenotrophomonsa meltophilia
NCBI PubMed ID: 8721742Journal NLM ID: 0043535Publisher: Elsevier
Institutions: School of Chemistry, University of Hull, Hull HU6 7RX, UK
Methods: NMR, chemical 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
Expand this compound
Collapse this compound
5. Compound ID: 833
| Cyclic
-3)-a-D-Fucp4NAc-(1-4)-b-D-ManpNAc-(1-4)-a-D-GlcpNAc-(1- |
Show graphically |
Structure type: cyclic polymer repeating unit
; n=4, 2430
Trivial name: Enterobacterial common antigen
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531,IEDB_885813
The structure is contained in the following publication(s):
- Article ID: 230
Erbel PJ, Barr K, Gao N, Gerwig GJ, Rick PD, Gardner KH "Identification and biosynthesis of cyclic enterobacterial common antigen in Escherichia coli" -
Journal of Bacteriology 185(6) (2003) 1995-2004
Phosphoglyceride-linked enterobacterial common antigen (ECA(PG)) is a cell surface glycolipid that is synthesized by all gram-negative enteric bacteria. The carbohydrate portion of ECA(PG) consists of linear heteropolysaccharide chains comprised of the trisaccharide repeat unit Fuc4NAc-ManNAcA-GlcNAc, where Fuc4NAc is 4-acetamido-4,6-dideoxy-D-galactose, ManNAcA is N-acetyl-D-mannosaminuronic acid, and GlcNAc is N-acetyl-D-glucosamine. The potential reducing terminal GlcNAc residue of each polysaccharide chain is linked via phosphodiester linkage to a phosphoglyceride aglycone. We demonstrate here the occurrence of a water-soluble cyclic form of enterobacterial common antigen, ECA(CYC), purified from Escherichia coli strains B and K-12 with solution nuclear magnetic resonance (NMR) spectroscopy, electrospray ionization mass spectrometry (ESI-MS), and additional biochemical methods. The ECA(CYC) molecules lacked an aglycone and contained four trisaccharide repeat units that were nonstoichiometrically substituted with up to four O-acetyl groups. ECA(CYC) was not detected in mutant strains that possessed null mutations in the wecA, wecF, and wecG genes of the wec gene cluster. These observations corroborate the structural data obtained by NMR and ESI-MS analyses and show for the first time that the trisaccharide repeat units of ECA(CYC) and ECA(PG) are assembled by a common biosynthetic pathway.
NMR, biosynthesis, antigen, common, chemistry, Bacterial, genetics, growth & development, metabolism, potential, strain, Non-U.S.Gov't, terminal, polysaccharide, trisaccharide, carbohydrate, cell, chain, linked, form, Escherichia, Escherichia coli, acid, antigens, immunology, enterobacterial common antigen, bacteria, electrospray, spectrometry, linkage, common antigen, cyclic, enterobacterial, identification, biochemistry, Magnetic Resonance Spectroscopy, nuclear, nuclear magnetic resonance, resonance, spectroscopy, surface, Gram-negative, mutation, purified, methods, glycolipid, reducing, heteropolysaccharide, linear, occurrence, phosphodiester, solution, Enterobacteriaceae, U.S.Gov't, electrophoresis, isolation & purification, Mass, Electrospray Ionization, P.H.S., Research Support, Basic Helix-Loop-Helix Transcription Factors, Trans-Activators, Transcription Factors
NCBI PubMed ID: 12618464Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: Kevin.Gardner@UTSouthwestern.edu
Institutions: Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, Texas 75390-9038, USA, Department of Pharmacology, University of Texas Southwestern Medical Center, Dallas, Texas 75390-9038, Department of Microbiology and Immunology, F. Edward Herbert School of Medicine, Uniformed Services University of the Health Sciences, Bethesda, Maryland 208142, Department of Bio-Organic Chemistry, Bijvoet Center, Utrecht University, 3508 TB Utrecht, The Netherlands
Methods: NMR, ESI-MS, FACE
Expand this compound
Collapse this compound
6. Compound ID: 912
|
EtN-(1--P--7)--+
|
a-L-Rhap-(1-4)-a-D-Glcp-(1-2)-L-gro-a-D-manHepp-(1-3)-+ | P-4)-+
| | |
R-3HOBut-(1-4)-a-D-Fucp4N-(1-4)-a-Legp5Ac7Ac-(2-6)-b-D-Glcp-(1-4)-D-gro-a-D-manHepp-(1-5)-Kdop-(2--/lipid A/
|
EtN-(1--P--2)--+ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_136105,IEDB_137777,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_2189046,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 262
Holst O "On the occurrence of D-glycero-D-manno-heptose in lipopolysaccharides" -
Polish Journal of Chemistry 73 (1999) 1055-1067
Lipopolysaccharides (LPS) consist of three regions, i.e. the lipid A, the core region, and the O-specific polysaccharide. The core region and the lipid A represent a common structural unit occurring in all LPS. The structures of the core region of various bacteria have been investigated intensively for the past ten years, and several core regions containing D-glycero-D-manno-heptose which is the biosynthetic precursor of the common core constituent L-glycero-D-manno-heptose have been identified. In this review, these core structures are summarized and briefly discussed.
Lipopolysaccharide, lipopolysaccharides, core, D-glycero-D-manno-heptose, composition, occurrence
Journal NLM ID: 7901356WWW link: http://www.ichf.edu.pl/pjch/pj-1999/pj0799.htm#1055Publisher: Państwowe Wydawnictwo Naukowe
Institutions: Research Center Borstel, Center for Medicine and Biosciences, 23845 Borstel, Germany
Expand this compound
Collapse this compound
7. Compound ID: 1815
| Cyclic
-3)-a-D-Fucp4NAc-(1-4)-b-D-ManpNAcA-(1-4)-a-D-GlcpNAc-(1- |
Show graphically |
Structure type: cyclic polymer repeating unit
; n=4-6
Trivial name: Enterobacterial common antigen
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 570
Erbel PJ, Seidel R, Macintosh SE, Gentile LN, Amor JC, Kahn RA, Prestegard JH, McIntosh LP, Gardner KH "Cyclic enterobacterial common antigen: Potential contaminant of bacterially expressed protein preparations" -
Journal of Biomolecular NMR 29(2) (2004) 199-204
We have previously reported the identification of the cyclic enterobacterial common antigen (ECA(CYC)) polysaccharide in E. coli strains commonly used for heterologous protein expression (PJA Erbel et al., J. Bacteriol. 185 (2003): 1995). Following this initial report, interactions among several NMR groups established that characteristic N -acetyl signals of ECA(CYC) have been observed in (15)N-(1)H HSQC spectra of samples of various bacterially-expressed proteins suggesting that this water-soluble carbohydrate is a common contaminant. We provide NMR spectroscopic tools to recognize ECA(CYC) in protein samples, as well as several methods to remove this contaminant. Early recognition of ECA-based NMR signals will prevent time-consuming analyses of this copurifying carbohydrate.
NMR, polysaccharide, enterobacterial common antigen, cyclic
NCBI PubMed ID: 15014233Journal NLM ID: 9110829Publisher: ESCOM Science Publishers
Correspondence: Kevin.Gardner@UTSouthwestern.edu
Institutions: Departments of Biochemistry and Pharmacology, University of Texas Southwestern Medical Center, Dallas TX 75390-9038, U.S.A
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, ESI-MS, 15N NMR
Expand this compound
Collapse this compound
8. Compound ID: 2080
|
R-3HOBut-(1-4)-a-D-Fucp4N-(1-4)-+
|
-3)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-4)-b-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_141807,IEDB_144988,IEDB_144989,IEDB_151528,IEDB_151531,IEDB_190606,SB_173,SB_21,SB_7
The structure is contained in the following publication(s):
- Article ID: 686
Haseley SR, Holst O, Brade H "Structural and serological characterisation of the O-antigenic polysaccharide of the lipopolysaccharide from Acinetobacter strain 90 belonging to DNA group 10" -
European Journal of Biochemistry 245(2) (1997) 470-476
Water-soluble lipopolysaccharide (phenol/water extraction) isolated from Acinetobacter strain 90, which belongs to DNA group 10, was hydrolysed with 1% acetic acid, ultracentrifuged, and water-soluble products finally eluted from a Sephadex G-50 column. The major fraction, a polysaccharide, contained D-Gal, D-GlcNAc, D-GalNAc, and 4,6-dideoxy-4-[(R)-3-hydroxybutyramido]-D-galactose (Fuc4NBuOH). The polysaccharide was characterised by means of monosaccharide analyses, Smith-degradation, N-deacetylation/deamination, and NMR studies, and was shown to have a branched pentasaccharide repeating unit. [structure in text] This structure was specifically recognised in western blots and enzyme immunoassays by polyclonal rabbit antisera.
Lipopolysaccharide, O-antigen, Acinetobacter
NCBI PubMed ID: 9151981Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Division of Medical and Biochemical Microbiology, Research Centre Borstel, Centre for Medicine and Biosciences, Germany.
Methods: NMR, Smith degradation, de-N-acetylation/deamination
- 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
Expand this compound
Collapse this compound
9. Compound ID: 2350
|
L-Orn-(5-6)-+ D-Asp-(1-4)-+
| |
-4)-b-D-GlcpNAc3NAcA-(1-4)-b-D-ManpNAc3NA-(1-3)-b-D-GlcpNAc-(1-3)-a-D-Fucp4N-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: polysaccharide part of a glycoconjugate, glycan repeating unit of the glycoconjugate
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 806
Hashimoto M, Asai Y, Jinno T, Adachi S, Kusumoto S "Structural elucidation of polysaccharide part of glycoconjugate from Treponema medium ATCC700293" -
European Journal of Biochemistry 270 (2003) 2671-2679
Glycoconjugates are distributed on the cell surfaces of some small-sized treponemes and have been reported to be completely different from lipopolysaccharides. We separated a glycoconjugate fraction from Treponema medium ATCC700293, a medium-sized oral spirochete, to assess its immunobiological activities and elucidate the chemical structure of its polysaccharide part using phenol/water extraction, hydrophobic chromatography, and gel .ltration. The glycoconjugate showed negligible or weak endotoxic and immunobiological properties. The chemical structure of the polysaccharide part was shown by two-dimensional NMR and MALDI-TOF-MS to be a tetrasaccharide backbone with two amino acids: -4)[Ac(1-3),Ac(1-2)]bDGlcpN3NA(1-4)[xLOrn(6-6)Ac(1-2)]bDManpN3NA(1-3)[Ac(1-2)]bDGlcpN(1-3)[xDAsp?(1-4)]aDFucp4N(1-.
structural, polysaccharide, aspartic acid, MALDI-TOF MS, ornithine, glycoconjugate, medium, Treponema
NCBI PubMed ID: 12787034Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: tomo527@dent.asahi-u.ac.jp
Institutions: Department of Oral Microbiology, Asahi University School of Dentistry, Gifu, Japan, Graduate School of Science, Osaka University, Osaka, Japan
Methods: NMR-2D, ESI-MS, MALDI-TOF MS
- Article ID: 3697
Harvey DJ "Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: An update for 2003-2004" -
Mass Spectrometry Reviews 28(2) (2009) 273-361
This review is the third update of the original review, published in 1999, on the application of matrix-assisted laser desorption/ionization (MALDI) mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings the topic to the end of 2004. Both fundamental studies and applications are covered. The main topics include methodological developments, matrices, fragmentation of carbohydrates and applications to large polymeric carbohydrates from plants, glycans from glycoproteins and those from various glycolipids. Other topics include the use of MALDI MS to study enzymes related to carbohydrate biosynthesis and degradation, its use in industrial processes, particularly biopharmaceuticals and its use to monitor products of chemical synthesis where glycodendrimers and carbohydrate-protein complexes are highlighted
carbohydrates, glycosyltransferases, fragmentation, MALDI, glycolipids, glycoproteins, biopharmaceuticals, glycosidases, time-of-flight
NCBI PubMed ID: 18825656Publication DOI: 10.1002/mas.2019Journal NLM ID: 8219702Publisher: Wiley
Correspondence: david.harvey@bioch.ox.ac.uk
Institutions: Department of Biochemistry, Oxford Glycobiology Institute, University of Oxford, Oxford OX1 3QU, UK
Methods: NMR, MALDI-TOF MS
- Article ID: 6301
Qin CJ, Ding MR, Tian GZ, Zou XP, Fu JJ, Hu J, Yin J "Chemical approaches towards installation of rare functional groups in bacterial surface glycans" -
Chinese Journal of Natural Medicines = Zhongguo Tianran Yaowu 20(6) (2022) 401-420
Bacterial surface glycans perform a diverse and important set of biological roles, and have been widely used in the treatment of bacterial infectious diseases. The majority of bacterial surface glycans are decorated with diverse rare functional groups, including amido, acetamidino, carboxamido and pyruvate groups. These functional groups are thought to be important constituents for the biological activities of glycans. Chemical synthesis of glycans bearing these functional groups or their variants is essential for the investigation of structure-activity relationships by a medicinal chemistry approach. To date, a broad choice of synthetic methods is available for targeting the different rare functional groups in bacterial surface glycans. This article reviews the structures of naturally occurring rare functional groups in bacterial surface glycans, and the chemical methods used for installation of these groups.
chemical synthesis, acetamidino group, amido group, bacterial surface glycan, carboxamido group, pyruvyl ketal
NCBI PubMed ID: 35750381Publication DOI: 10.1016/S1875-5364(22)60177-8Journal NLM ID: 101504416Publisher: Beijing: Science Press; Elsevier
Correspondence: J. Yin
Institutions: Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, China, Wuxi School of Medicine, Jiangnan University, Wuxi, China
Expand this compound
Collapse this compound
10. Compound ID: 2427
|
L-Orn-(5-6)-+ D-Asp-(1-4)-+
| |
b-D-GlcpNAc3NAcA-(1-4)-b-D-ManpNAc3NA-(1-3)-b-D-GlcpNAc-(1-3)-D-Fucp4N |
Show graphically |
Structure type: oligomer
Trivial name: repeating unit of the glycoconjugate polysaccharide part
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 806
Hashimoto M, Asai Y, Jinno T, Adachi S, Kusumoto S "Structural elucidation of polysaccharide part of glycoconjugate from Treponema medium ATCC700293" -
European Journal of Biochemistry 270 (2003) 2671-2679
Glycoconjugates are distributed on the cell surfaces of some small-sized treponemes and have been reported to be completely different from lipopolysaccharides. We separated a glycoconjugate fraction from Treponema medium ATCC700293, a medium-sized oral spirochete, to assess its immunobiological activities and elucidate the chemical structure of its polysaccharide part using phenol/water extraction, hydrophobic chromatography, and gel .ltration. The glycoconjugate showed negligible or weak endotoxic and immunobiological properties. The chemical structure of the polysaccharide part was shown by two-dimensional NMR and MALDI-TOF-MS to be a tetrasaccharide backbone with two amino acids: -4)[Ac(1-3),Ac(1-2)]bDGlcpN3NA(1-4)[xLOrn(6-6)Ac(1-2)]bDManpN3NA(1-3)[Ac(1-2)]bDGlcpN(1-3)[xDAsp?(1-4)]aDFucp4N(1-.
structural, polysaccharide, aspartic acid, MALDI-TOF MS, ornithine, glycoconjugate, medium, Treponema
NCBI PubMed ID: 12787034Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: tomo527@dent.asahi-u.ac.jp
Institutions: Department of Oral Microbiology, Asahi University School of Dentistry, Gifu, Japan, Graduate School of Science, Osaka University, Osaka, Japan
Methods: NMR-2D, ESI-MS, MALDI-TOF MS
Expand this compound
Collapse this compound
11. Compound ID: 3463
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
The structure is contained in the following publication(s):
- Article ID: 1320
Zdorovenko GM, Gvozdyak RI, Gubanova NY, Afonina GB, Zdorovenko EL "Characteristics of the lipopolysaccharide from Pseudomonas fluorescens" -
Mikrobiologiia = Microbiology [Russian] 68(3) (1999) 281-289
Lipopolysaccharide of Pseudomonas fluorescens strain IMV 7769 (biovar I) was isolated and investigated. Fractions of the structural parts of the LPS macromolecule, lipid A, the core oligosaccharide, and O-specific polysaccharide, were obtained in a homogeneous state. 2-Hydroxydecanoic, 3-hydroxydecanoic, dodecanoic, 2-hyrdroxydodecanoic, 3-hydroxydodecanoic, hexadecanoic, octadecanoic, hexadecenoic, and octadecenoic fatty acids, phosphoethanolamine, glucosamine, and three unindentified peaks forming a separate cluster together with glucosamine were found. Lipid A was shown to be phosphorylated. Glucose, fucose, rhamnose, glucoseamine, galactoseamine, two unidentified amino sugards, 2-keto-3-deoxyoctulonic acid (Kdo), heptose, ethanolamine, phosphoethanolamine, and alanine were identified in the core oligosaccharide. OPS of LPS consisted of repeating trisaccharide fragments that included residues of amino sugars: 4-acetamido-4,6-dideoxy-D-galactose, 2-acetamido-2,6-dideoxy-D-glucose, and 2-acetamido-2,6-dideoxy-L-glucose. During growth, the strain under study, exerted exocellular LPS into the medium. The LPS studied was similar to the LPS of the earlier investigated strains P. fluorescens (biovar I) IMV 1152 and IMV 1433 in the structure of OPS, but differed from them in the composition of both lipid A and the core oligosaccharide. The LPS of the strain studied differed from LPS of the type strain P. fluorescens IMV 4125 (ATCC13525) in all characteristics determined.
Lipopolysaccharide, structure, core, lipid A, O-chain, Pseudomonas fluorescens
Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: zdorov@i.kiev.ua
Institutions: Institute of Microbiology and Virology, National Academy of Science of Ukraine, Kiev, Ukaine, National Medical University, Kiev, Ukraine, Shevchenko University, Kiev, Ukraine
Methods: methylation, GLC-MS, NMR-2D, NMR
- 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: 2254
Knirel YA, Paramonov NA, Shashkov AS, Kochetkov NK, Zdorovenko GM, Veremeychenko SN, Zakharova IY "Somatic antigens of pseudomonads: structure of the O-specific polysaccharide of Pseudomonas fluorescens biovar A strain IMV 1152" -
Carbohydrate Research 243 (1993) 205-210
No abstract available
NCBI PubMed ID: 8324763Publication DOI: 10.1016/0008-6215(93)84093-lJournal NLM ID: 0043535Publisher: Elsevier
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow
Methods: 13C NMR, 1H NMR, NMR-2D, GLC
- 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
Expand this compound
Collapse this compound
12. Compound ID: 3575
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
The structure is contained in the following publication(s):
- Article ID: 1322
Zdorovenko GM, Veremeichenko SN "Comparative characteristics of lipopolysaccharides of various Pseudomonas fluorescens strains (biovar I)" -
Mikrobiologiia = Microbiology [Russian] 70(4) (2001) 441-450
From the biomass of five Pseudomonas fluorescens biovar I strains, including the P. fluorescens type strain IMV 4125 (ATCC13525), lipopolysaccharides (LPS) were isolated (by extraction with a phenol- water mixture followed by repeated ultracentrifugation), as well as individual structural components of the LPS macromolecule: lipid A, the core oligosaccharide, and O-specific polysaccharide (O-PS). 3- Hydroxydecanoic, 2-hydroxydodecanoic, 3-hydroxydodecanoic, dodecanoic, hexadecanoic, octadecanoic, hexadecenoic, and octadecenoic fatty acids were present in lipid A of the LPS of all the strains studied. Glucosamine, ethanolamine, and phosphoethanolamine were revealed in the lipid A hydrophilic part of all of KDO, a trace amount of heptoses, ethanolamine, phosphoethanolamine, alanine, and phosphorus were identified as the main core components. Interstrain differences in the core oligosaccharide composition were revealed. Structural analysis showed that the O-PS of the type strain, as distinct from that of other strains, is heterogeneous and contains two types of repetitive units, including (1) three L-rhamnose residues (L-Rha), one 3-acetamide-3,6-dideoxy-D-galactose residue (D-Fuc3NAc) as a branching substitute of the L-rhamnan chain and (2) three L-Rha residues and two branching D- Fuc3NAc residues. The type strain is also serologically distinct from other biovar I strains due to the LPS O-chain structure, which is similar to those of the strains of the species Pseudomonas syringae, including the type strain. The data of structural analysis agree well with the results of immunochemical studies of LPS.
Lipopolysaccharide, structure, lipid A, core oligosaccharide, O-specific polysaccharide, Pseudomonas fluorescens, serological cross reactivity
NCBI PubMed ID: 11558277Publication DOI: 10.1023/A:1010486211742Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Correspondence: zdorov@i.kiev.ua
Institutions: Zabolotnyi Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, ul. Zabolotnogo 154, Kiev, 252143 Ukraine
- Article ID: 3583
Veremeichenko SN, Zdorovenko GM "Specific structural features and immunomodulatory properties of the lipopolysaccharides of Pseudomonas bacteria" -
Applied Biochemistry and Microbiology 44(6) (2008) 571-579
The results of in vitro studies of the immunomodulatory action of the lipopolysaccharides (LPS) of the Pseudomonas bacteria— P. fluorescens biovar I strains IMV 4125 = ATCC 13525, IMV 7769, and IMV 1152; P. fluorescens biovar IV strain IMV 2111; P. syringae pv. syringae IMV 281 = CPPB 281 = ATCC 19310 and IMV 467; and P. wieringae IMV 7923—on the mouse spleenocytes and human peripheral blood mononuclear cells (PBMC), B lymphocytes, and T lymphocytes are described. The proliferative activity of mouse spleenocytes correlated with the degree of LPS toxicity. The PBMC mitogenic activity induced by the P. fluorescens IMV 7769 LPS preparation exceeded the activity of E. coli 026: B6 LPS. The immunomodulatory effect of LPS on T cells was strain and dose dependent. The LPS of P. syringae pv. syringae INV 467 displayed a comparatively pronounced immunomodulatory effect on human blood B lymphocytes.
lipopolysaccharides, structural, Pseudomonas, specific, immunomodulatory
NCBI PubMed ID: 19145969Journal NLM ID: 0042510Publisher: Kluwer Academic/Plenum Publishers
Correspondence: stas@diapr.kiev.ua
Institutions: Research and Production Company Diaprof-Med, Kiev, 04123 Ukraine, Zabolotny Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, 02143 Ukraine
Methods: serological methods
Expand this compound
Collapse this compound
13. Compound ID: 3646
Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 1365
Barr K, Klena J, Rick PD "The modality of enterobacterial common antigen polysaccharide chain lengths is regulated by o349 of the wec gene cluster of Escherichia coli K-12" -
Journal of Bacteriology 181(20) (1999) 6564-6568
antigen, common, gene, polysaccharide, chain, Escherichia, Escherichia coli, enterobacterial common antigen, cluster, gene cluster, common antigen, enterobacterial, chain length
Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: Rick@usuhs.mil
Institutions: Department of Microbiology and Immunology, Uniformed Services University of the Health Sciences, Bethesda, MD
Methods: genetic methods
Expand this compound
Collapse this compound
14. Compound ID: 3811
|
a-D-Fucp4NAc2Me-(1-4)-b-D-GlcpA-(1-4)-a-L-Fucp2Me-(1-3)-a-L-Rhap-(1-2)-a-L-6dTalp-(1-3)-D-aThr-(?--/N-acylpeptide LIP(1-2)xDPhe(1-2)xDaThr(1-2)xDAla?(1-2)Subst // Subst = alaninol = SMILES N{2}[C@@H](C){1}CO/ |
Show graphically |
Structure type: oligomer
Aglycon: N-acylpeptide LIP(1-2)xDPhe(1-2)xDaThr(1-2)xDAla?(1-2)Subst // Subst = alaninol = SMILES N{2}[C@@H](C){1}CO
Trivial name: oligosaccharide hapten
Compound class: glycopeptidolipid (GPL)
Contained glycoepitopes: IEDB_115136,IEDB_136045,IEDB_136105,IEDB_140630,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_423153,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 1451
Chatterjee D, Khoo KH "The surface glycopeptidolipids of mycobacteria: structures and biological properties" -
Cellular and Molecular Life Sciences 58(14) (2001) 2018-2042
One of the most important opportunistic pathogens associated with acquired immunodeficiency syndrome (AIDS) is the M. avium complex. M. avium infections are found in up to 70% of individuals in advanced stages of AIDS. It is apparent that M. avium can replicate in host macrophages and persist for long periods. This group of mycobacteria are distinguished by the presence of unique, highly antigenic, surface- located lipids known as the glycopeptidolipids (GPLs). The GPLs are the chemical basis of the 31 distinct serovars of the M. avium complex, and have also been identified in some other species. The M. avium lipids are immunosuppressive and can induce a variety of cytokines that affect general host responses. Despite extensive chemical characterization of the structures of these GPLs, much work is needed to elucidate the molecular mechanism involved in this complex glycosylation pathway and its genetic basis. The challenges for the future lie in explaining the roles of these copious products in the intracellular life and infectivity of mycobacteria. The intention of our review is to offer a concise account of the structures of the M. avium lipids, their putative roles in the host responses, bacterial physiology and pathogenesis, particularly in immunocompromised patients such as those infected with human immunodeficiency virus (HIV). Advances in chemical synthesis of the various haptenic oligosaccharides are also given to demonstrate how these have helped to define the immunogenic determinants. We believe that future research should involve the creation of conditional mutants defective in these lipids for both functional and biosynthesis studies which will complement biological assays using chemically defined or modified neoglycoconjugates
Mycobacteria, neoglycoproteins, glycopeptidolipid (GPL), Mycobacterium avium complex (MAC), haptenic oligosaccharides
NCBI PubMed ID: 11814054Publication DOI: 10.1007/PL00000834Journal NLM ID: 9705402Publisher: Basel: Springer
Correspondence: delphi@lamar.colostate.edu
Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523, USA, Institute of Biological Chemistry, Academia Sinica, Taipei (Taiwan)
Expand this compound
Collapse this compound
15. Compound ID: 3978
|
EtN-(1--P--7)--+
|
a-L-Rhap-(1-4)-a-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-3)-+ | P-4)-+
| | |
R-3HOBut-(1-4)-a-D-Fucp4N-(1-4)-a-Legp5Am7Ac-(2-6)-b-D-Glcp-(1-4)-D-gro-a-D-manHepp-(1-5)-Kdo
|
EtN-(1--P--2)--+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_136105,IEDB_137777,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_2189046,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 1470
Knirel YA, Shashkov AS, Tsvetkov YE, Jansson P, Zähringer U "5,7-Diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids in bacterial glycopolymers: chemistry and biochemistry" -
Book: Advances in Carbohydrate Chemistry and Biochemistry (2003) Vol. 58, 371-417
This chapter provides an overview of the chemistry of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids in bacterial glycopolymers. Ald-2-ulosonic acids are the important components of natural glycoconjugates. Sialic acids—namely, N- and O-acyl derivatives of 5-amino-3,5-dideoxy-D-glycero-D-galacto-non-2-ulosonic acid (neuraminic acid, Neu), generally occur in glycoconjugates of vertebrates and play a significant role in their recognition, regulation, and protection. A deamino analogue of neuraminic acid—3-deoxy-D-glycero-D-galacto-non-2-ulosonic acid (Kdn)—has also been found in a variety of animal tissues. 3-Deoxy-D-manno-oct-2-ulosonic acid (Kdo) is an essential component of lipopolysaccharides (LPSs) of Gram-negative bacteria that functions to link the carbohydrate portion to the lipid moiety. In rare cases, Kdo in LPS is replaced with a 3-hydroxylated analogue—D-glycero-D-talo-oct-2-ulosonic acid. The chapter focuses on the occurrence and characterization of derivatives of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids and presents experimental approaches that are used to identify them and to elucidate the structures of the bacterial polysaccharides that contain the nonulosonic acids. It also presents the recent data on the biosynthesis of these sugars and discusses their role in immune recognition.
Lipopolysaccharide, LPS, structure, polysaccharide, Bacterial polysaccharide, 5, 7-diamino-3, 7, higher sugar, 9-tetradeoxynonulosonic acid
NCBI PubMed ID: 14719362Publication DOI: 10.1016/S0065-2318(03)58007-6Publisher: Elsevier Inc.
Correspondence: knirel@ioc.ac.ru
Editors: Horton D
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany, Karolinska Institute, Clinical Research Center, Huddinge University Hospital, Huddinge, Sweden
Expand this compound
Collapse this compound
Next 15 structure(s)
Total list of structure IDs on all result pages of the current query:
Total list of corresponding CSDB IDs (permanent record IDs):
Execution: 1 sec