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1. Compound ID: 33
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-4)-a-D-GalpNAcA3Ac6NH2-(1-4)-a-D-GalpNFoA6NH2-(1-3)-a-D-QuipNAc-(1-2)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 12
Belanger M, Burrows LL, Lam JS "Functional analysis of genes responsible for the synthesis of the B-band O antigen of Pseudomonas aeruginosa serotype O6 lipopolysaccharide" -
Microbiology 145(12) (1999) 3505-3521
This study reports the organization of the wbp gene cluster and characterization of a number of genes that are essential for B-band O antigen biosynthesis in the clinically prevalent Pseudomonas aeruginosa serotype 06. Twelve genes were identified that share homology with other LPS and polysaccharide biosynthetic genes. This cluster contains homologues of wzx (encoding the O antigen flippase/translocase) and wzz (which modulates O antigen chain length distribution) genes, typical of a wzy-dependent pathway. However, a complete wzy gene (encoding the O-polymerase) was not found within the cluster. Four biosynthetic genes, wbpO, wbpP, wbpV and wbpM, and four putative glycosyltransferase genes, wbpR, wbpT, wbpU and wbpL, were identified in the cluster. To characterize their roles in LPS biosynthesis, null mutants of wbpO, wbpP, wbpV, wbpL and wbpM were generated using a gene-replacement strategy. Mutations in each of these genes caused deficiency in B-band synthesis. The wbpL mutant was deficient in both A-band and B-band LPS. WbpL(O6) is a bi-functional enzyme which could initiate B-band synthesis through the addition of QuiNAc to undecaprenol phosphate, and A-band synthesis by transferring either a GalNAc or a GlcNAc residue. Another approach used to assign function to the wbp(O6) genes was by complementation analysis. Two genes from Salmonella typhi, wcdA and wcdB, responsible for the synthesis of a homopolymer of GalNAcA called Vi antigen were used in complementation experiments to verify the functions of wbpO and wbpP. wcdA and wcdB restored B-band synthesis in wbpO and wbpP mutants respectively, implying that wbpO and wbpP are involved in UDP-GalNAcA synthesis. Although wbpV has homology to wbpK of the serotype O5 B-band LPS synthesis cluster, complementation analysis using the respective null mutants showed that the genes are not interchangeable. A knockout mutation of wbpN (located downstream of wbpM) did not abrogate LPS synthesis in either 05 or 06; therefore, it has been renamed orf48.5. These results establish the organization of genes involved in P. aeruginosa B-band O antigen synthesis and provide the evidence to assign functions to a number of LPS biosynthetic genes
Lipopolysaccharide, synthesis, antigen, functional, gene, serotype, O-antigen, analysis, B-band, O antigen, Pseudomonas, Pseudomonas aeruginosa
NCBI PubMed ID: 10627048Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: jlam@uoguelph.ca
Institutions: Department of Microbiology, University of Guelph, Canada, N1G 2W1
Methods: PCR, DNA sequencing, DNA cloning
- Article ID: 515
Vinogradov E, Conlan WJ, Gunn JS, Perry MB "Characterization of the lipopolysaccharide O-antigen of Francisella novicida (U112)" -
Carbohydrate Research 339(3) (2004) 649-654
Francisella novicida (U112), a close relative of the highly virulent bacterium F. tularensis, was shown to produce a lipopolysaccharide in which the antigenic O-polysaccharide component was found by chemical, (1)H and (13)C NMR and MS analyses to be an unbranched neutral linear polymer of a repeating tetrasaccharide unit composed of 2-acetamido-2-deoxy-d-galacturonamide (d-GalNAcAN) and 2,4-diacetamido-2,4,6-trideoxy-d-glucose (d-Qui2NAc4NAc, di-N-acetylbacillosamine) residues (3:1) and had the structure: [Formula: see text] With polyclonal murine antibody, the F. novicida O-antigen did not show serological cross-reactivity with the O-antigen of F. tularensis despite the occurrence of a common →4)-d-GalpNAcAN-(1→4)-α-D-GalpNAcAN-(1→ disaccharide unit in their respective O-antigens. Thus, O-PS serology offers a practical way to distinguish between the two Francisella species.
Lipopolysaccharide, NMR, structure, common, tetrasaccharide, characterization, O-antigen, O antigen, polymer, Research, antibodies, antibody, O-polysaccharide, O antigens, O polysaccharide, O-antigens, bacteria, neutral, serological, serology, biological, chemical, antigenic, component, MS, disaccharide, linear, occurrence, lipopolysaccharide O-antigen, species, cross-reactivity, crossreactivity, virulent, PDF, murine
NCBI PubMed ID: 15013402Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: malcolm.perry@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada K1A OR6, Department of Virology, Immunology and Medical Genetics, Department of Medicine, Division of Infectious Diseases, The Center for Microbial Interface Biology, The Ohio State University, Columbus, OH, USA
Methods: methylation, NMR-2D, NMR, sugar analysis, MS
- Article ID: 2091
Vinogradov EV, Knirel YA, Shashkov AS, Kochetkov NK "Determination of the degree of amidation of 2-deoxy-2-formamido-D-galacturonic acid in O-specific polysaccharides of Pseudomonas aeruginosa O4 and related strains" -
Carbohydrate Research 170 (1987) C1-C4
Journal NLM ID: 0043535Publisher: Elsevier
Methods: 13C NMR
- Article ID: 2193
Vinogradov EV, Shashkov AS, Knirel YA, Kochetkov NK, Tochtamysheva NV, Averin SF, Goncharova OV, Khlebnikov VS "Structure of the O-antigen of Francisella tularensis strain 15" -
Carbohydrate Research 214 (1991) 289-297
The O-specific polysaccharide, obtained by mild acid degradation of the lipopolysaccharide of Francisella tularensis strain 15, contained 2-acetamido-2,6-dideoxy-D-glucose (D-QuiNAc), 4,6-dideoxy-4-formamido-D-glucose (D-Qui4NFm), and 2-acetamido-2-deoxy-D-galacturonamide (D-GalNAcAN) in the ratios 1:1:2. Tri- and tetra-saccharide fragments were obtained on treatment of the polysaccharide with anhydrous hydrogen fluoride and partial hydrolysis with 0.1 M hydrochloric acid, respectively. On the basis of 1H- and 13C-n.m.r. spectroscopy of the polysaccharide and the saccharides, it was concluded that the O-antigen had the structure: →4)-α-D-GalpNAcAN-(1→4)-α-D-GalpNAcAN-(1→3)-β-D-QuipNAc-(1→2)-β-D-Quip4NFm-(1→. This O-antigen is related in structure to those of Pseudomonas aeruginosa O6, immunotype 1, and IID 1008, and Shigella dysenteriae type 7.
NCBI PubMed ID: 1769021Publication DOI: 10.1016/0008-6215(91)80036-mJournal NLM ID: 0043535Publisher: Elsevier
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the U.S.S.R., Moscow
Methods: 13C NMR, 1H NMR, partial acid hydrolysis, HF solvolysis, sugar analysis, GLC, deamination, GPC, NaBH4 reduction
- Article ID: 3711
King JD, Kocincova D, Westman EL, Lam JS "Lipopolysaccharide biosynthesis in Pseudomonas aeruginosa" -
Innate Immunity 15(5) (2009) 261-312
Pseudomonas aeruginosa causes serious nosocomial infections, and an important virulence factor produced by this organism is lipopolysaccharide (LPS). This review summarizes knowledge about biosynthesis of all three structural domains of LPS - lipid A, core oligosaccharide, and O polysaccharides. In addition, based on similarities with other bacterial species, this review proposes new hypothetical pathways for unstudied steps in the biosynthesis of P. aeruginosa LPS. Lipid A biosynthesis is discussed in relation to Escherichia coli and Salmonella, and the biosyntheses of core sugar precursors and core oligosaccharide are summarised. Pseudomonas aeruginosa attaches a Common Polysaccharide Antigen and O-Specific Antigen polysaccharides to lipid A-core. Both forms of O polysaccharide are discussed with respect to their independent synthesis mechanisms. Recent advances in understanding O-polysaccharide biosynthesis since the last major review on this subject, published nearly a decade ago, are highlighted. Since P. aeruginosa O polysaccharides contain unusual sugars, sugar-nucleotide biosynthesis pathways are reviewed in detail. Knowledge derived from detailed studies in the O5, O6 and O11 serotypes is applied to predict biosynthesis pathways of sugars in poorly-studied serotypes, especially O1, O4, and O13/O14. Although further work is required, a full understanding of LPS biosynthesis in P. aeruginosa is almost within reach.
Lipopolysaccharide, core, O-antigen, Pseudomonas aeruginosa, lipid A
NCBI PubMed ID: 19710102Publication DOI: 10.1177/1753425909106436Journal NLM ID: 101469670Publisher: Sage Publications
Correspondence: jlam@uoguelph.ca
Institutions: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario, Canada
- Article ID: 3869
Kabanov DS, Prokhorenko IR "Structural analysis of lipopolysaccharides from Gram-negative bacteria" -
Biochemistry (Moscow) 75(4) (2010) 383-404
This review covers data on composition and structure of lipid A, core, and O-polysaccharide of the known lipopolysaccharides from Gram-negative bacteria. The relationship between the structure and biological activity of lipid A is discussed. The data on roles of core and O-polysaccharide in biological activities of lipopolysaccharides are presented. The structural homology of some oligosaccharide sequences of lipopolysaccharides to gangliosides of human cell membranes is considered.
core, Lipooligosaccharide, O-antigen, lipid A, gangliosides, cytokines, lipopolysaccharide (endotoxin)
NCBI PubMed ID: 20618127Publication DOI: 10.1134/S0006297910040012Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: kabanovd1@rambler.ru
Institutions: Institute of Basic Biological Problems, Russian Academy of Sciences, Pushchino, Russia
- Article ID: 5461
Knirel YA, Naumenko OI, Senchenkova SN, Perepelov AV "Chemical methods for selective cleavage of glycosidic linkages in structural analysis of bacterial polysaccharides" -
Russian Chemical Reviews = Uspekhi Khimii 88(4) (2019) 406-424
This review is devoted to methods for the selective cleavage of glycosidic bonds. The mechanisms of reactions underlying these methods are considered and examples of their practical application in the structural analysis of bacterial polysaccharides are given. Specific methods for the selective cleavage of polysaccharides, remaining relevant for researchers, include the Smith degradation based on destruction of monosaccharides containing vicinal diol groups, dephosphorylation of phosphate-containing polysaccharides with hydrofluoric acid and the hydrolytic cleavage of glycosyl phosphate bonds in the latter compounds. Non-specific methods, including partial acid hydrolysis, acetolysis and solvolysis with anhydrous organic (CF3SO3H, MeSO3H, CF3CO2H) and inorganic (HF) acids do not make any specific demands on the composition and structure of the polysaccharide and are sensitive to its fine structural features. The review addesses the issue of stability of glycosidic bonds in various monosaccharides to reagents used for non-specific selective cleavage.
structural analysis, Bacterial polysaccharide, selective cleavage, glycosidic bond
Publication DOI: 10.1070/RCR4856Journal NLM ID: 0404506Publisher: London: Chemical Society
Correspondence: Yu.A. Knirel
Institutions: N.D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences
Methods: partial acid hydrolysis, HF solvolysis, acid hydrolysis, mild acid hydrolysis, alkaline degradation, b-elimination, Smith degradation, deamination, de-O-acetylation, HF treatment, reduction with NaBD4, triflic acid solvolysis, acetolysis, Li/ethylenediamine degradation, hydrazinolysis, reduction with NaBH4, mild acid degradation, trifluoroacetic acid solvolysis, partial solvolysis with trifluoroacetic acid, de-N-acetylation with hydrazine, part acid hydrolysis, HF solvolysis; published polymerization frame was shifted for conformity with other records.
- Article ID: 5835
Richard G, MacKenzie CR, Henry KA, Vinogradov E, Hall JC, Hussack G "Antibody Binding to the O-Specific Antigen of Pseudomonas aeruginosa O6 Inhibits Cell Growth" -
Antimicrobial Agents and Chemotherapy 64(4) (2020) e02168
Pseudomonas aeruginosa is an opportunistic pathogen that is inherently resistant to many antibiotics and represents an increasing threat due to the emergence of drug-resistant strains. There is a pressing need to develop innovative antimicrobials against this pathogen. In this study we identified the O-specific antigen (OSA) of P. aeruginosa serotype O6 as a novel target for therapeutic intervention. Binding of monoclonal antibodies and antigen-binding fragments therefrom to O6 OSA leads to rapid outer membrane destabilization and inhibition of cell growth. The antimicrobial effect correlated directly with antibody affinity. Antibody binding to the O-antigen of a second lipopolysaccharide type present in P. aeruginosa or to the LPS core did not affect cell viability. Atomic force microscopy showed that antibody binding to OSA resulted in early flagellum loss, formation of membrane blebs, and eventually complete outer membrane loss. We hypothesize that antibody binding to OSA disrupts a key interaction in the P. aeruginosa outer membrane.
Lipopolysaccharide, LPS, AFM, atomic force microscopy, antibacterial antibodies, O-specific antigen, outer membrane disruption
NCBI PubMed ID: 32015038Publication DOI: 10.1128/AAC.02168-19Journal NLM ID: 0315061Correspondence: Greg.Hussack@nrc-cnrc.gc.ca
Institutions: School of Environmental Sciences, University of Guelph, Guelph, ON, Canada N1G 2W1, Department of Biochemistry, Microbiology and Immunology, University of Ottawa, Ottawa, ON, Canada K1H 8M5, Human Health Therapeutics Research Centre, National Research Council Canada, Ottawa, ON, Canada K1A 0R6
Methods: ELISA, serological methods, SPR, AFM, antibody sequence analyses
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2. Compound ID: 142
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a-D-Glcp-(1-4)-+
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a-D-Glcp-(1-6)-+ | P-6)-+ P-2)-+ a-Kdop-(2-4)-+
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a-L-Rhap-(1-4)-a-D-GalpNAcA3Ac6NH2-(1-4)-a-D-GalpNFoA6NH2-(1-3)-b-D-QuipNAc-(1-3)-a-L-Rhap-(1-3)-b-D-Glcp-(1-3)-a-D-GalpN-(1-3)-L-gro-a-D-manHepp7Cm-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
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L-Ala-(1-2)-+ P-4)-+ |
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Structure type: oligomer
Aglycon: lipid A
Trivial name: glycoform 2 core oligosaccharide with O-unit
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_1330403,IEDB_136105,IEDB_137473,IEDB_140088,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_189517,IEDB_2189047,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 30
Bystrova OV, Shashkov AS, Kocharova NA, Knirel YA, Lindner B, Zähringer U, Pier GB "Structural studies on the core and the O-polysaccharide repeating unit of Pseudomonas aeruginosa immunotype 1 lipopolysaccharide" -
European Journal of Biochemistry 269(8) (2002) 2194-2203
The structure of the lipopolysaccharide (LPS) of Pseudomonas aeruginosa immunotype 1 was studied after mild acid and strong alkaline degradations by MS and NMR spectroscopy. Three types of LPS molecules were found, including those with an unsubstituted glycoform 1 core (A) or an isomeric glycoform 2 core substituted with one O-polysaccharide repeating unit (B) or with a long-chain O-polysaccharide. Therefore, of two core glycoforms, only glycoform 2 accepts the O-polysaccharide. In the structures A and B, Kdo, Hep, Hep7Cm, GalNAcAN3Ac, GalNFoAN, QuiNAc, GalNAla represent 3-deoxy-d-manno-octulosonic acid, l-glycero-d-manno-heptose, 7-O-carbamoyl-l-glycero-d-manno-heptose, 2-acetamido-3-O-acetyl-2-deoxygalacturonamide, 2-formamido-2-deoxygalacturonamide, 2-acetamido-2,6-dideoxyglucose and 2-(l-alanylamino)-2-deoxygalactose, respectively; all sugars are in the pyranose form and have the d configuration unless otherwise stated. One or more phosphorylation sites may be occupied by diphosphate groups. In a minority of the LPS molecules, an O-acetyl group is present in the outer core region at unknown position. The site and the configuration of the linkage between the O-polysaccharide and the core and the structure of the O-polysaccharide repeating unit were defined in P. aeruginosa immunotype 1. The QuiNAc residue linked to the Rha residue of the core was found to have the beta configuration, whereas in the interior repeating units of the O-polysaccharide this residue is in the α-configuration. The data obtained are in accordance with the initiation of biosynthesis of the O-polysaccharide of P. aeruginosa O6, which is closely related to immunotype 1, by transfer of d-QuiNAc-1-P to undecaprenyl phosphate followed by synthesis of the repeating O-antigen tetrasaccharide
Lipopolysaccharide, structure, repeating unit, Pseudomonas aeruginosa, core oligosaccharide, O-polysaccharide
NCBI PubMed ID: 11985598Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany, Channing Laboratory, Department of Medicine, Brigham and Women's Hospital, Harvard Medical School, Boston, MA, USA
Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR, ESI-MS, GLC, mild acid hydrolysis, alkaline degradation
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3. Compound ID: 145
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-2)-a-L-Rhap-(1-4)-a-D-GalpNAcA3Ac6NH2-(1-4)-a-D-GalpNFoA6NH2-(1-3)-a-D-QuipNAc-(1- |
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Structure type: polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 30
Bystrova OV, Shashkov AS, Kocharova NA, Knirel YA, Lindner B, Zähringer U, Pier GB "Structural studies on the core and the O-polysaccharide repeating unit of Pseudomonas aeruginosa immunotype 1 lipopolysaccharide" -
European Journal of Biochemistry 269(8) (2002) 2194-2203
The structure of the lipopolysaccharide (LPS) of Pseudomonas aeruginosa immunotype 1 was studied after mild acid and strong alkaline degradations by MS and NMR spectroscopy. Three types of LPS molecules were found, including those with an unsubstituted glycoform 1 core (A) or an isomeric glycoform 2 core substituted with one O-polysaccharide repeating unit (B) or with a long-chain O-polysaccharide. Therefore, of two core glycoforms, only glycoform 2 accepts the O-polysaccharide. In the structures A and B, Kdo, Hep, Hep7Cm, GalNAcAN3Ac, GalNFoAN, QuiNAc, GalNAla represent 3-deoxy-d-manno-octulosonic acid, l-glycero-d-manno-heptose, 7-O-carbamoyl-l-glycero-d-manno-heptose, 2-acetamido-3-O-acetyl-2-deoxygalacturonamide, 2-formamido-2-deoxygalacturonamide, 2-acetamido-2,6-dideoxyglucose and 2-(l-alanylamino)-2-deoxygalactose, respectively; all sugars are in the pyranose form and have the d configuration unless otherwise stated. One or more phosphorylation sites may be occupied by diphosphate groups. In a minority of the LPS molecules, an O-acetyl group is present in the outer core region at unknown position. The site and the configuration of the linkage between the O-polysaccharide and the core and the structure of the O-polysaccharide repeating unit were defined in P. aeruginosa immunotype 1. The QuiNAc residue linked to the Rha residue of the core was found to have the beta configuration, whereas in the interior repeating units of the O-polysaccharide this residue is in the α-configuration. The data obtained are in accordance with the initiation of biosynthesis of the O-polysaccharide of P. aeruginosa O6, which is closely related to immunotype 1, by transfer of d-QuiNAc-1-P to undecaprenyl phosphate followed by synthesis of the repeating O-antigen tetrasaccharide
Lipopolysaccharide, structure, repeating unit, Pseudomonas aeruginosa, core oligosaccharide, O-polysaccharide
NCBI PubMed ID: 11985598Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany, Channing Laboratory, Department of Medicine, Brigham and Women's Hospital, Harvard Medical School, Boston, MA, USA
Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR, ESI-MS, GLC, mild acid hydrolysis, alkaline degradation
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4. Compound ID: 148
Structure type: polymer biological repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130422,IEDB_130667,IEDB_136105,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 31
Bystrova OV, Shashkov AS, Kocharova NA, Knirel YA, Zähringer U, Pier GB "Elucidation of the structure of the lipopolysaccharide core and the linkage between the core and the O-antigen in Pseudomonas aeruginosa immunotype 5 using strong alkaline degradation of the lipopolysaccharide" -
Biochemistry (Moscow) 68(8) (2003) 918-925
The products of the strong alkaline degradation of the lipopolysaccharide (LPS) of Pseudomonas aeruginosa immunotype 5 were separated by anion-exchange HPLC and studied by electrospray ionization mass spectrometry and NMR spectroscopy. It was found that two major products have the same inner core region and lipid A carbohydrate backbone but different outer core regions. The difference is in the position of a rhamnose residue, which is substituted with either an additional glucose residue or a disaccharide remainder of the degraded O-polysaccharide. The site and the configuration of the linkage between the O-polysaccharide and the core were determined and, together with published data, the structure of the so-called biological repeating unit of the O-antigen was defined. The glycosidic linkage of the 2-acetamido-2,6-dideoxy-D-glucose (N-acetyl-D-quinovosamine) residue is ? when it links the O-polysaccharide to the core and ? when it connects the interior repeating units of the O-polysaccharide to each other
Lipopolysaccharide, O-antigen, repeating unit, Pseudomonas aeruginosa, core oligosaccharide
NCBI PubMed ID: 12948393Publication DOI: 10.1023/a:1025759217501Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Research Center Borstel, Center for Medicine and Biosciences, Borstel, Germany, Channing Laboratory, Department of Medicine, Brigham and Women's Hospital, Harvard Medical School, Boston, MA, USA
Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR, ESI-MS, GLC, alkaline degradation
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5. Compound ID: 159
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a-D-GlcpN-(1-7)-+
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a-D-GlcpA-(1-2)-L-gro-a-D-manHepp-(1-3)-+
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a-D-GalpNA-(1-6)-+ |
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L-gro-a-D-manHepp-(1-4)-+ | | EtN-(1--P--4)--+
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a-D-GlcpNAc-(1-4)-b-D-ManpNAc3NAcA-(1-3)-b-L-FucpNAc4NMe-(1-6)-a-D-GlcpN-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_115136,IEDB_120354,IEDB_123890,IEDB_130650,IEDB_137340,IEDB_137777,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140630,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_2275071,IEDB_2275073,IEDB_2275074,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 36
Caroff M, Brisson J, Martin A, Karibian D "Structure of the Bordetella pertussis 1414 endotoxin" -
FEBS Letters 477 (2000) 8-14
The endotoxin (lipopolysaccharide) of Bordetella pertussis, the agent of whooping cough, consists of a lipid A linked to a highly branched dodecasaccharide containing several acid and amino sugars. The elucidation of the polysaccharide structure was accomplished by first analyzing the structures of fragments obtained by hydrolysis and nitrous deamination and then piecing the fragments together. The fine structure of the antigenic distal pentasaccharide, presented here, was determined by chemical analyses as well as by high-resolution nuclear magnetic resonance and mass spectrometry. The complete structure was reconstituted and confirmed by matrix-assisted laser desorption/ionization mass spectrometry. The following structure was derived from the combined experimental data:The detailed structure combined with previously reported serological data now allows the synthesis of its epitopes for potential vaccines
structure, Bordetella, Bordetella pertussis, endotoxin, pertussis
NCBI PubMed ID: 10899302Publication DOI: 10.1016/s0014-57930001720-8Journal NLM ID: 0155157Publisher: Elsevier
Correspondence: martine.caroff@bbmpc.u-psud.fr
Institutions: Equipe Endotoxines, UMR 8619 du Centre National de la Recherche Scientifique, Biochimie, Universite de Paris- Sud, F-91405, Orsay, France
Methods: 13C NMR, 1H NMR, NMR-2D, conformation analysis, GC, b-elimination, Smith degradation, MALDI-MS
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6. Compound ID: 171
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a-D-GlcpN-(1-7)-+
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a-D-GlcpA-(1-2)-L-gro-a-D-manHepp-(1-3)-+
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a-D-GalpNA-(1-6)-+ |
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L-gro-a-D-manHepp-(1-4)-+ | | EtN-(1-0)-?%P-4)-+
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a-D-GlcpNAc-(1-4)-b-D-ManpNAc3NAcA-(1-3)-b-L-FucpNAc4NMe-(1-6)-a-D-GlcpN-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_115136,IEDB_120354,IEDB_123890,IEDB_130650,IEDB_137340,IEDB_137777,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140630,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_2275071,IEDB_2275073,IEDB_2275074,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 37
Caroff M, Karibian D "Structure of bacterial lipopolysaccharides" -
Carbohydrate Research 338(23) (2003) 2431-2447
Bacterial lipopolysaccharides are the major components of the outer surface of Gram-negative bacteria They are often of interest in medicine for their immunomodulatory properties. In small amounts they can be beneficial, but in larger amounts they may cause endotoxic shock. Although they share a common architecture, their structural details exert a strong influence on their activity. These molecules comprise: a lipid moiety, called lipid A, which is considered to be the endotoxic component, a glycosidic part consisting of a core of approximately 10 monosaccharides and, in 'smooth-type' lipopolysaccharides, a third region, named O-chain, consisting of repetitive subunits of one to eight monosaccharides responsible for much of the immunospecificity of the bacterial cell.
Lipopolysaccharide, structure, core, lipid A, endotoxin, O-chains
NCBI PubMed ID: 14670707Publication DOI: 10.1016/j.carres.2003.07.010Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: martine.carloff@bbmpc.u-psud.fr
Institutions: Equipe Endotoxines, UMR 8619 du Centre National de la Recherche Scientifique, IBBMC, Université de Paris-Sud, F-Orsay, France
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7. Compound ID: 434
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S-3HOBut-(1-4)-+ S-3HOBut-(1-3)-+
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-2)-a-L-Rhap-(1-4)-a-D-GalpNAcA-(1-3)-a-D-QuipNAc4N-(1-2)-b-D-Quip3N-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 160
Veremeychenko SN, Zdorovenko GM "Peculiarity of the structure of the lipopolysaccharide of Pseudomonas fluorescens IMV 247 (biovar II)" -
Mikrobiologiia = Microbiology [Russian] 69(3) (2000) 362-369
The results of the study of the Pseudomonas fluorescens IMV 247 (biovar II) lipopolysaccharide (LPS) isolated from the dry bacterial mass by Westphal's method and purified by repeated ultracentrifugation are presented. The macromolecular organization of the LPS is characterized by the presence of S and R forms of LPS molecules in a 1:1 ratio. The structural components of the LPS molecule → lipid A, the core oligosaccharide, and the O-specific polysaccharide -- were isolated and characterized. 3-Hydroxydecanoic, 2-hydroxydodecanoic, 3-hydroxydodecanoic, and dodecanoic acids proved to be the main lipid A fatty acids. Glucosamine, phosphoethanolamine, and phosphorus were identified as the components of the lipid A hydrophilic portion. Glucose, galactose, arabinose, rhamnose, glucosamine, alanine, phosphoethanolamine, phosphorus, and 2-keto-3-deoxyoctulonate (KDO) were revealed in the heterogeneous fraction of the core oligosaccharide. The O-specific polysaccharide chain was composed of repeating tetrasaccharide units consisting of L-rhamnose (L-Rha), 3,6-dideoxy-3-[(S)-3-hydroxybutyramido]-D-glucose (D-Qui3NHb), 2-acetamido-2,4,6-trideoxy-4[(S)-3-hydroxybutyramido-D-glucose (D-QuiNAc4NHb), and 2-acetamido-2-deoxy-D-galacturonic acid (D-GalNAcA) residues. A peculiarity of the O-specific polysaccharide was that it released, upon partial acid hydrolysis, the nonreducing disaccharide GalNAcA → QuiNAc4NHb with a 3-hydroxybutyryl group glycosylated intramolecularly with a QuiN4N residue. Double immunodiffusion in agar and lipopolysaccharide precipitation reactions revealed no serological interrelationship between the strain studied and the P. fluorescens strains studied earlier.
Lipopolysaccharide, LPS, structure, strain, characterization, Pseudomonas, fatty acid, O-chain, biovar, Pseudomonas fluorescens
NCBI PubMed ID: 10920806Journal NLM ID: 0376652Publisher: Moskva: Izdatelstvo Nauka
Institutions: Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, Kiev, Ukraine.
Methods: NMR-2D, NMR
- 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: 4335
Kondakova AN, Novototskaya-Vlasova KA, Shashkov AS, Drutskaya MS, Senchenkova SN, Shcherbakova VA, Gilichinsky DA, Nedospasov SA, Knirel YA "Structure of an acidic polysaccharide isolated from Psychrobacter maritimus 3pS containing a bacillosamine derivative" -
Carbohydrate Research 359 (2012) 7-10
An acidic polysaccharide was obtained from Psychrobacter maritimus 3pS isolated from a Siberian cryopeg sample (Kolyma lowland). The following structure of the tetrasaccharide repeating unit of the polysaccharide was established by sugar analysis along with (1)H and (13)C NMR spectroscopy: →2)-α-L-Rhap-(1→4)-α-D-GalpNAcA-(1→3)-α-D-QuipNAc4NHb-(1→3)-β-D-QuipNAc4NHb-(1→ where D-GalNAcA indicates 2-acetamido-2-deoxy-D-galacturonic acid and d-QuiNAc4NHb indicates 2-acetamido-2,4,6-trideoxy-4-[(S)-3-hydroxybutanoyl]amino-D-glucose.
acid, bacterial polysaccharide structure, 2, 4, 4-diamino-2, 2-acetamido-2-deoxy-D-galacturonic acid, Psychrobacter maritimus, 6-trideoxy-D-glucopyranose
NCBI PubMed ID: 22925757Publication DOI: 10.1016/j.carres.2012.07.007Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: annakond@gmail.com
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute for Physicochemical and Biological Problems in Soil Science, Russian Academy of Sciences, 142290 Pushchino, Russia, Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow, Russia, Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences,142290 Pushchino, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, ESI-MS, GLC, mild acid hydrolysis, DOC-PAGE, Smith degradation, GPC
- 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
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8. Compound ID: 559
|
a-D-GlcpN-(1-7)-+
|
b-D-GlcpA-(1-2)-L-gro-a-D-manHepp-(1-3)-+
| |
P-4)-+ |
|
a-D-GalpNA-(1-6)-+ | P-4)-+ P-4)-+
| | | |
?%Sugp-(1-3)-b-D-FucpN(%)Ac4N-(1-6)-a-D-GlcpN-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
Sug = 2,3-diamino-2,3,4-trideoxy-hex-4-enuronopyranosyl = SMILES O{1}C1[C@H](N)C(N)=C[C@@H](C(O)=O)O1 |
Show graphically |
Structure type: oligomer
Compound class: LPS
Contained glycoepitopes: IEDB_115136,IEDB_130650,IEDB_135394,IEDB_137777,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140630,IEDB_140956,IEDB_141807,IEDB_142345,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_423153,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 171
Vinogradov E "The structure of the carbohydrate backbone of the lipopolysaccharides from Bordetella hinzii and Bordetella bronchiseptica" -
European Journal of Biochemistry 267(14) (2000) 4577-4582
The structure of the core-lipid A region of the lipopolysaccharides from Bordetella hinzii and Bordetella bronchiseptica has been analyzed. Lipopolysaccharides were deacylated using strong alkaline hydrolysis, the products were separated by high performance anion-exchange chromatography and analyzed by NMR and mass spectrometry. The following structure of the products can be deduced from the experimental results: where for the product from Bordetella hinzii N = H, R = H, β-FucN4N- or partially N-acetylated Sug-(1-3)-β-FucN4N and for the product from Bordetella bronchiseptica N = α-Hep, R = H, β-FucN4N, β-FucN4NMe or partially N-acetylated Sug-(1-3)-β-FucN4N or Sug-(1-3)-β-FucN4NMe; Sug = 2,3-diamino-2,3,4-trideoxy-hex-4-enuronopyranosyl.
lipopolysaccharides, Bordetella, Bordetella bacteria, Bordetella bronchiseptica, Bordetella hinzii, lipid structure
NCBI PubMed ID: 10880983Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada
Methods: NMR-2D, NMR, MS, HPLC, alkaline hydrolysis
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9. Compound ID: 560
|
a-D-GlcpN-(1-4)-+
|
a-D-GalpNA-(1-6)-b-D-Glcp-(1-4)-+
|
a-D-GlcpN-(1-7)-+ | P-4)-+ P-4)-+
| | | |
b-D-GlcpA-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
|
P-4)-+ |
Show graphically |
Structure type: oligomer
Compound class: LPS
Contained glycoepitopes: IEDB_115136,IEDB_130650,IEDB_135394,IEDB_137777,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140630,IEDB_140956,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_423153,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 171
Vinogradov E "The structure of the carbohydrate backbone of the lipopolysaccharides from Bordetella hinzii and Bordetella bronchiseptica" -
European Journal of Biochemistry 267(14) (2000) 4577-4582
The structure of the core-lipid A region of the lipopolysaccharides from Bordetella hinzii and Bordetella bronchiseptica has been analyzed. Lipopolysaccharides were deacylated using strong alkaline hydrolysis, the products were separated by high performance anion-exchange chromatography and analyzed by NMR and mass spectrometry. The following structure of the products can be deduced from the experimental results: where for the product from Bordetella hinzii N = H, R = H, β-FucN4N- or partially N-acetylated Sug-(1-3)-β-FucN4N and for the product from Bordetella bronchiseptica N = α-Hep, R = H, β-FucN4N, β-FucN4NMe or partially N-acetylated Sug-(1-3)-β-FucN4N or Sug-(1-3)-β-FucN4NMe; Sug = 2,3-diamino-2,3,4-trideoxy-hex-4-enuronopyranosyl.
lipopolysaccharides, Bordetella, Bordetella bacteria, Bordetella bronchiseptica, Bordetella hinzii, lipid structure
NCBI PubMed ID: 10880983Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada
Methods: NMR-2D, NMR, MS, HPLC, alkaline hydrolysis
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10. Compound ID: 561
|
a-D-GlcpN-(1-7)-+
|
b-D-GlcpA-(1-2)-L-gro-a-D-manHepp-(1-3)-+
| |
P-4)-+ |
|
a-D-GalpNA-(1-6)-+ | P-4)-+ P-4)-+
| | | |
b-D-FucpN4N-(1-6)-a-D-GlcpN-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P |
Show graphically |
Structure type: oligomer
Compound class: LPS
Contained glycoepitopes: IEDB_115136,IEDB_130650,IEDB_135394,IEDB_137777,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140630,IEDB_140956,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_423153,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 171
Vinogradov E "The structure of the carbohydrate backbone of the lipopolysaccharides from Bordetella hinzii and Bordetella bronchiseptica" -
European Journal of Biochemistry 267(14) (2000) 4577-4582
The structure of the core-lipid A region of the lipopolysaccharides from Bordetella hinzii and Bordetella bronchiseptica has been analyzed. Lipopolysaccharides were deacylated using strong alkaline hydrolysis, the products were separated by high performance anion-exchange chromatography and analyzed by NMR and mass spectrometry. The following structure of the products can be deduced from the experimental results: where for the product from Bordetella hinzii N = H, R = H, β-FucN4N- or partially N-acetylated Sug-(1-3)-β-FucN4N and for the product from Bordetella bronchiseptica N = α-Hep, R = H, β-FucN4N, β-FucN4NMe or partially N-acetylated Sug-(1-3)-β-FucN4N or Sug-(1-3)-β-FucN4NMe; Sug = 2,3-diamino-2,3,4-trideoxy-hex-4-enuronopyranosyl.
lipopolysaccharides, Bordetella, Bordetella bacteria, Bordetella bronchiseptica, Bordetella hinzii, lipid structure
NCBI PubMed ID: 10880983Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada
Methods: NMR-2D, NMR, MS, HPLC, alkaline hydrolysis
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11. Compound ID: 562
|
a-D-GlcpN-(1-7)-+
|
b-D-GlcpA-(1-2)-L-gro-a-D-manHepp-(1-3)-+
| |
P-4)-+ |
|
a-D-GalpNA-(1-6)-+ | P-4)-+ P-4)-+
| | | |
?%Sug-(1-3)-b-D-FucpN4N(%)Ac-(1-6)-a-D-GlcpN-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
Sug = 2,3-diamino-2,3,4-trideoxy-hex-4-enuronopyranose = SMILES O{1}C1[C@H](N)C(N)=C[C@@H](C(O)=O)O1 |
Show graphically |
Structure type: oligomer
Compound class: LPS
Contained glycoepitopes: IEDB_115136,IEDB_130650,IEDB_135394,IEDB_137777,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140630,IEDB_140956,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_423153,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 171
Vinogradov E "The structure of the carbohydrate backbone of the lipopolysaccharides from Bordetella hinzii and Bordetella bronchiseptica" -
European Journal of Biochemistry 267(14) (2000) 4577-4582
The structure of the core-lipid A region of the lipopolysaccharides from Bordetella hinzii and Bordetella bronchiseptica has been analyzed. Lipopolysaccharides were deacylated using strong alkaline hydrolysis, the products were separated by high performance anion-exchange chromatography and analyzed by NMR and mass spectrometry. The following structure of the products can be deduced from the experimental results: where for the product from Bordetella hinzii N = H, R = H, β-FucN4N- or partially N-acetylated Sug-(1-3)-β-FucN4N and for the product from Bordetella bronchiseptica N = α-Hep, R = H, β-FucN4N, β-FucN4NMe or partially N-acetylated Sug-(1-3)-β-FucN4N or Sug-(1-3)-β-FucN4NMe; Sug = 2,3-diamino-2,3,4-trideoxy-hex-4-enuronopyranosyl.
lipopolysaccharides, Bordetella, Bordetella bacteria, Bordetella bronchiseptica, Bordetella hinzii, lipid structure
NCBI PubMed ID: 10880983Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada
Methods: NMR-2D, NMR, MS, HPLC, alkaline hydrolysis
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12. Compound ID: 563
|
a-D-GlcpN-(1-7)-+
|
b-D-GlcpA-(1-2)-L-gro-a-D-manHepp-(1-3)-+
| |
P-4)-+ |
|
a-D-GalpNA-(1-6)-+ | P-4)-+ P-4)-+
| | | |
b-D-FucpN4N-(1-6)-L-gro-a-D-manHepp-(1-4)-a-D-GlcpN-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P |
Show graphically |
Structure type: oligomer
Compound class: LPS
Contained glycoepitopes: IEDB_115136,IEDB_130650,IEDB_135394,IEDB_137777,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140630,IEDB_140956,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_423153,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 171
Vinogradov E "The structure of the carbohydrate backbone of the lipopolysaccharides from Bordetella hinzii and Bordetella bronchiseptica" -
European Journal of Biochemistry 267(14) (2000) 4577-4582
The structure of the core-lipid A region of the lipopolysaccharides from Bordetella hinzii and Bordetella bronchiseptica has been analyzed. Lipopolysaccharides were deacylated using strong alkaline hydrolysis, the products were separated by high performance anion-exchange chromatography and analyzed by NMR and mass spectrometry. The following structure of the products can be deduced from the experimental results: where for the product from Bordetella hinzii N = H, R = H, β-FucN4N- or partially N-acetylated Sug-(1-3)-β-FucN4N and for the product from Bordetella bronchiseptica N = α-Hep, R = H, β-FucN4N, β-FucN4NMe or partially N-acetylated Sug-(1-3)-β-FucN4N or Sug-(1-3)-β-FucN4NMe; Sug = 2,3-diamino-2,3,4-trideoxy-hex-4-enuronopyranosyl.
lipopolysaccharides, Bordetella, Bordetella bacteria, Bordetella bronchiseptica, Bordetella hinzii, lipid structure
NCBI PubMed ID: 10880983Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada
Methods: NMR-2D, NMR, MS, HPLC, alkaline hydrolysis
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13. Compound ID: 564
|
a-D-GlcpN-(1-7)-+
|
b-D-GlcpA-(1-2)-L-gro-a-D-manHepp-(1-3)-+
| |
P-4)-+ |
|
a-D-GalpNA-(1-6)-+ | P-4)-+ P-4)-+
| | | |
b-D-FucpN4N(%)Me-(1-6)-a-D-GlcpN-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P |
Show graphically |
Structure type: oligomer
Compound class: LPS
Contained glycoepitopes: IEDB_115136,IEDB_130650,IEDB_135394,IEDB_137777,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140630,IEDB_140956,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_423153,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 171
Vinogradov E "The structure of the carbohydrate backbone of the lipopolysaccharides from Bordetella hinzii and Bordetella bronchiseptica" -
European Journal of Biochemistry 267(14) (2000) 4577-4582
The structure of the core-lipid A region of the lipopolysaccharides from Bordetella hinzii and Bordetella bronchiseptica has been analyzed. Lipopolysaccharides were deacylated using strong alkaline hydrolysis, the products were separated by high performance anion-exchange chromatography and analyzed by NMR and mass spectrometry. The following structure of the products can be deduced from the experimental results: where for the product from Bordetella hinzii N = H, R = H, β-FucN4N- or partially N-acetylated Sug-(1-3)-β-FucN4N and for the product from Bordetella bronchiseptica N = α-Hep, R = H, β-FucN4N, β-FucN4NMe or partially N-acetylated Sug-(1-3)-β-FucN4N or Sug-(1-3)-β-FucN4NMe; Sug = 2,3-diamino-2,3,4-trideoxy-hex-4-enuronopyranosyl.
lipopolysaccharides, Bordetella, Bordetella bacteria, Bordetella bronchiseptica, Bordetella hinzii, lipid structure
NCBI PubMed ID: 10880983Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada
Methods: NMR-2D, NMR, MS, HPLC, alkaline hydrolysis
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14. Compound ID: 565
|
a-D-GlcpN-(1-7)-+
|
b-D-GlcpA-(1-2)-L-gro-a-D-manHepp-(1-3)-+
| |
P-4)-+ |
|
a-D-GalpNA-(1-6)-+ | P-4)-+ P-4)-+
| | | |
?%Sug-(1-3)-b-D-FucpN(%)Ac4N-(1-6)-L-gro-a-D-manHepp-(1-4)-a-D-GlcpN-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
Sug = 2,3-diamino-2,3,4-trideoxy-hex-4-enuronopyranose = SMILES O{1}C1[C@H](N)C(N)=C[C@@H](C(O)=O)O1 |
Show graphically |
Structure type: oligomer
Compound class: LPS
Contained glycoepitopes: IEDB_115136,IEDB_130650,IEDB_135394,IEDB_137777,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140630,IEDB_140956,IEDB_141807,IEDB_142345,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_423153,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 171
Vinogradov E "The structure of the carbohydrate backbone of the lipopolysaccharides from Bordetella hinzii and Bordetella bronchiseptica" -
European Journal of Biochemistry 267(14) (2000) 4577-4582
The structure of the core-lipid A region of the lipopolysaccharides from Bordetella hinzii and Bordetella bronchiseptica has been analyzed. Lipopolysaccharides were deacylated using strong alkaline hydrolysis, the products were separated by high performance anion-exchange chromatography and analyzed by NMR and mass spectrometry. The following structure of the products can be deduced from the experimental results: where for the product from Bordetella hinzii N = H, R = H, β-FucN4N- or partially N-acetylated Sug-(1-3)-β-FucN4N and for the product from Bordetella bronchiseptica N = α-Hep, R = H, β-FucN4N, β-FucN4NMe or partially N-acetylated Sug-(1-3)-β-FucN4N or Sug-(1-3)-β-FucN4NMe; Sug = 2,3-diamino-2,3,4-trideoxy-hex-4-enuronopyranosyl.
lipopolysaccharides, Bordetella, Bordetella bacteria, Bordetella bronchiseptica, Bordetella hinzii, lipid structure
NCBI PubMed ID: 10880983Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada
Methods: NMR-2D, NMR, MS, HPLC, alkaline hydrolysis
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15. Compound ID: 566
|
a-D-GlcpN-(1-7)-+
|
b-D-GlcpA-(1-2)-L-gro-a-D-manHepp-(1-3)-+
| |
P-4)-+ |
|
a-D-GalpNA-(1-6)-+ | P-4)-+ P-4)-+
| | | |
?%Sug-(1-3)-b-D-FucpN(%)Ac4N(%)Me-(1-6)-L-gro-a-D-manHepp-(1-4)-a-D-GlcpN-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2-6)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
Sug = 2,3-diamino-2,3,4-trideoxy-hex-4-enuronopyranose = SMILES O{1}C1[C@H](N)C(N)=C[C@@H](C(O)=O)O1 |
Show graphically |
Structure type: oligomer
Compound class: LPS
Contained glycoepitopes: IEDB_115136,IEDB_130650,IEDB_135394,IEDB_137777,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140630,IEDB_140956,IEDB_141807,IEDB_142345,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_423153,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 171
Vinogradov E "The structure of the carbohydrate backbone of the lipopolysaccharides from Bordetella hinzii and Bordetella bronchiseptica" -
European Journal of Biochemistry 267(14) (2000) 4577-4582
The structure of the core-lipid A region of the lipopolysaccharides from Bordetella hinzii and Bordetella bronchiseptica has been analyzed. Lipopolysaccharides were deacylated using strong alkaline hydrolysis, the products were separated by high performance anion-exchange chromatography and analyzed by NMR and mass spectrometry. The following structure of the products can be deduced from the experimental results: where for the product from Bordetella hinzii N = H, R = H, β-FucN4N- or partially N-acetylated Sug-(1-3)-β-FucN4N and for the product from Bordetella bronchiseptica N = α-Hep, R = H, β-FucN4N, β-FucN4NMe or partially N-acetylated Sug-(1-3)-β-FucN4N or Sug-(1-3)-β-FucN4NMe; Sug = 2,3-diamino-2,3,4-trideoxy-hex-4-enuronopyranosyl.
lipopolysaccharides, Bordetella, Bordetella bacteria, Bordetella bronchiseptica, Bordetella hinzii, lipid structure
NCBI PubMed ID: 10880983Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: evguenii.vinogradov@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada
Methods: NMR-2D, NMR, MS, HPLC, alkaline hydrolysis
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