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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: 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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5. 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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6. 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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7. 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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8. 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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9. 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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10. 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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11. 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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12. 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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13. 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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14. 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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15. Compound ID: 728
|
a-L-FucpNAc-(1-4)-+
|
-3)-a-D-GalpNAcA-(1-3)-a-L-FucpNAc-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 194
Vinogradov EV, Pantophlet R, Dijkshoorn L, Brade L, Holst O, Brade H "Structural and serological characterisation of two O-specific polysaccharides of Acinetobacter" -
European Journal of Biochemistry 239 (1996) 602-610
Extraction of dry bacteria of Acinetobacter strain 34 (DNA group 2) or Acinetobacter strain 108 (DNA group 13) by phenol/water yielded a polymer that was identified by means of serological studies and fatty acid analysis as S-form lipopolysaccharide. Degradation of the lipopolysaccharides of strains 34 and 108 in 1% acetic acid and 5% acetic acid, respectively, and gel-permeation chromatography gave the respective O-antigenic polysaccharides, the structures of which were determined, by compositional analysis and NMR spectroscopy of the polysaccharide, as [Sequence: see text] for strain 108, where D-Fucp3NBuOH represents 3-[(R)-3-hydroxybutyramido] -3,6-dideoxy-D-galactose and D-GalpANAc represents 2-acetamido-2-deoxy-D-galacturonic acid. Both structures were specifically recognised in Western blots by polyclonal rabbit antisera and there was no cross-reaction between these two structures.
Lipopolysaccharide, NMR, Acinetobacter, serology, Western blot
NCBI PubMed ID: 8774703Publication DOI: 10.1111/j.1432-1033.1995.899_3.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Division of Biochemical Microbiology, Center for Medicine and Biosciences, Research Center Borstel, Germany, Department of Medical Microbiology, Leiden University Hospital, Leiden, The Netherlands
Methods: NMR-2D, NMR, composition analysis
- Article ID: 684
Haseley SR, Wilkinson SG "Structure of the O-specific polysaccharide of Acinetobacter baumannii O5 containing 2-acetamido-2-deoxy-D-galacturonic acid" -
European Journal of Biochemistry 237 (1996) 229-233
polysaccharide containing 2-acetamido-2-deoxy-D-glucose (GlcNAc), 2-acetamido-2-deoxy-L-fucose (FucNAc), and 2-acetamido-2-deoxy-D-galacturonic acid (GalNAcA) was isolated from an aqueous phenol extract of lipid-free, isolated cell walls of the reference strain for Acinetobacter baumannii serogroup O5, by mild acid hydrolysis of the extract and chromatography of the water-soluble products on Sephadex G-50. By means of NMR studies, methylation analysis, carboxyl reduction and chemical degradations, the repeating unit of the polymer was identified as a branched tetrasaccharide of the structure shown. The serologically active polymer is believed to correspond to the side chain of the O5 lipopolysaccharide: [table: see text]
structure, polysaccharide, acid, Acinetobacter, Acinetobacter baumannii, O-specific, O-specific polysaccharide, 2-acetamido-2, 6-dideoxy-L-galactose, 2-acetamido-2-deoxy-D-galacturonic acid
NCBI PubMed ID: 8620877Publication DOI: 10.1111/j.1432-1033.1996.0229n.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: School of Chemistry, University of Hull, England.
Methods: methylation, NMR-2D, partial acid hydrolysis, NMR, carboxyl reduction, Smith degradation
- 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: 4534
Hu D, Liu B, Dijkshoorn L, Wang L, Reeves PR "Diversity in the major polysaccharide antigen of Acinetobacter baumannii assessed by DNA sequencing, and development of a molecular serotyping scheme" -
PLoS One 8(7) (2013) e70329
We have sequenced the gene clusters for type strains of the Acinetobacter baumannii serotyping scheme developed in the 1990s, and used the sequences to better understand diversity in surface polysaccharides of the genus. We obtained genome sequences for 27 available serovar type strains, and identified 25 polysaccharide gene cluster sequences. There are structures for 12 of these polysaccharides, and in general the genes present are appropriate to the structure where known. This greatly facilitates interpretation. We also find 53 different glycosyltransferase genes, and for 7 strains can provisionally allocate specific genes to all linkages. We identified primers that will distinguish the 25 sequence forms by PCR or microarray, or alternatively the genes can be used to determine serotype by 'molecular serology'. We applied the latter to 190 Acinetobacter genome-derived gene-clusters, and found 76 that have one of the 25 gene-cluster forms. We also found novel gene clusters and added 52 new gene-cluster sequence forms with different wzy genes and different gene contents. Altogether, the strains that have one of the original 25 sequence forms include 98 A. baumannii (24 from our strains) and 5 A. nosocomialis (3 from our strains), whereas 32 genomes from 12 species other than A. baumannii or A. nosocomialis, all have new sequence forms. One of the 25 serovar type sequences is found to be in European clone I (EC I), 2 are in EC II but none in EC III. The public genome strains add an additional 52 new sequence forms, and also bring the number found in EC I to 5, in EC II to 9 and in EC III to 2.
antigen, structure, Acinetobacter baumannii, gene cluster, glycosyltransferase, serotyping, genome, surface polysaccharide, polysaccharide antigen
NCBI PubMed ID: 23922982Publication DOI: 10.1371/journal.pone.0070329Journal NLM ID: 101285081Publisher: San Francisco, CA: Public Library of Science
Correspondence: Peter R. Reeves
Institutions: TEDA School of Biological Sciences and Biotechnology, Nankai University, Tianjin, China, Department of Infectious Diseases, Leiden University Medical Center, Leiden, The Netherlands, School of Molecular Bioscience, University of Sydney, Sydney, Australia
Methods: PCR, DNA sequencing, DNA techniques, genetic methods
- Article ID: 4819
Giguere D "Surface polysaccharides from Acinetobacter baumannii: Structures and syntheses" -
Carbohydrate Research 418 (2015) 29-43
The emergence of multidrug-resistance Acinetobacter baumannii requires novel approaches for prevention, treatment and diagnosis. The structures of surface polysaccharides from A. baumannii are valuable tools to understand pathogenesis, virulence and immunogenicity. The synthesis of bacterial mono- or polysaccharides may result in novel probes to become important therapeutic options in the fight against A. baumannii. This report exemplifies the relevance of glycochemistry for the development of new antibiotics.
lipopolysaccharides, capsular polysaccharides, Acinetobacter, Acinetobacter baumannii, polysaccharide synthesis, surface polysaccharides
NCBI PubMed ID: 26531136Publication DOI: 10.1016/j.carres.2015.10.001Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: denis.giguere@chm.ulaval.ca
Institutions: Département de Chimie, Université Laval, Québec City, Québec, Canada G1V 0A6
- Article ID: 5791
Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.
polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component
Publication DOI: 10.1016/B978-0-12-819475-1.00005-5Publisher: Elsevier
Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
Editors: Barchi J, Kamerling H
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
- Article ID: 5792
Knirel YA, Shneider MM, Popova AV, Kasimova AA, Senchenkova SN, Shashkov AS, Chizhov AO "Mechanisms of Acinetobacter baumannii Capsular Polysaccharide Cleavage by Phage Depolymerases" -
Biochemistry (Moscow) 85(5) (2020) 567-574
Aerobic gram-negative bacterium Acinetobacter baumannii has recently become one of the most relevant pathogens associated with hospital-acquired infections worldwide. A. baumannii produces a capsule around the cell, which represents a thick viscous layer of structurally variable capsular polysaccharide (CPS). The capsule protects the bacteria against unfavorable environmental factors and biological systems, including bacteriophages and host immune system. Many A. baumannii phages have structural depolymerases (tailspikes) that specifically recognize and digest bacterial CPS. In this work, we studied the interaction of tailspike proteins of four lytic depolymerase-carrying phages with A. baumannii CPS. Depolymerases of three bacteriophages (Fri1, AS12, and BS46) were identified as specific glycosidases that cleave the CPS of A. baumannii strains 28, 1432, and B05, respectively, by the hydrolytic mechanism. The gp54 depolymerase from bacteriophage AP22 was characterized as a polysaccharide lyase that cleaves the CPS of A. baumannii strain 1053 by β-elimination at hexuronic acid (ManNAcA) residues.
Acinetobacter baumannii, capsular polysaccharide, NMR spectroscopy, bacteriophage, Polysaccharide lyase, Tailspike, depolymerase, glycosidase, hexuronic acid, receptor binding protein
NCBI PubMed ID: 32571186Publication DOI: 10.1134/S0006297920050053Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: yknirel@gmail.com
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, 142279, Russia, Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology of Russia, Moscow, Russia, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Moscow, Russia, Institute of Antimicrobial Chemotherapy, Smolensk State Medical University, Smolensk, 214019, Russia, Moscow Institute of Physics and Technology (National Research University), Dolgoprudny, Moscow Region, 141701, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, DNA techniques, GPC, enzymatic digestion, HR-ESI-MS
- Article ID: 6309
Rudenko N, Karatovskaya A, Zamyatina A, Shepelyakovskaya A, Semushina S, Brovko F, Shpirt A, Torgov V, Kolotyrkina N, Zinin A, Kasimova A, Perepelov A, Shneider M, Knirel Y "Immune Response to Conjugates of Fragments of the Type K9 Capsular Polysaccharide of Acinetobacter baumannii with Carrier Proteins" -
Microbiology Spectrum 10(5) (2022) e0167422
The clonal bacterial species Acinetobacter baumannii is an emerging multidrug-resistant pathogen which causes high-lethality infections. Cells of A. baumannii are surrounded by the type-specific capsular polysaccharide (CPS), which provides resistance to the protective mechanisms of the host and is considered a target for immunization. The conjugates of three inert carrier proteins and A. baumannii type K9 CPS fragments, which contained various numbers of oligosaccharide repeats (K-units), were synthesized by periodate oxidation and squaric acid chemistry. The conjugates were applied to immunize mice, and chemical synthesis by squaric acid was shown to significantly improve the immunogenic properties of glycoconjugate. In BALB/c mice, IgG antibodies were predominant among type K9 CPS reactive antibodies, and their total content was several times higher than that of IgM. Immune sera were characterized by their opsonization ability during practically the entire lives of the experimental mice. The sera were cross-reactive, but the highest specificity was observed against the antigen (type K9 CPS) used for immunization. The immunization of BALB/c and ICR-1 mice with a glycoconjugate without adjuvants led to varying degrees of stimulation of IL-10, IL-17A, and TNF-alpha production, but not IL-4 production in the ICR-1 mice. This is in contrast to the BALB/c mice, in which gamma-IFN production was also activated. The protective effectiveness of the glycoconjugates obtained by squaric acid chemistry was demonstrated by experiments that involved challenging immunized and nonimmunized animals with a lethal dose of A. baumannii K9. IMPORTANCE Immunization by glycoconjugates with A. baumannii type K9 CPS fragments induced a high level of antibodies (predominantly IgG) in sera, which reacted specifically with the CPS of A. baumannii type K9, as well as a long immunological memory. The sera of immunized animals efficiently opsonized A. baumannii type K9. Immunization resulted in the balanced production of pro/anti-inflammatory lymphokines and protective antibodies to ensure the survival of the mice infected with A. baumannii. The level of specific antibodies was sufficient to provide protective immunity against the challenge by A. baumannii, making this approach applicable in the development of vaccine preparations.
carbohydrates, carbohydrate, Acinetobacter baumannii, capsular polysaccharide, glycoconjugate, immunochemistry, interleukins, opsonisation assay
NCBI PubMed ID: 35980044Publication DOI: 10.1128/spectrum.01674-22Journal NLM ID: 101634614Publisher: Washington, DC: ASM Press
Correspondence: N.Rudenko
Institutions: Laboratory of Immunochemistry, Pushchino Branch, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Pushchino, Moscow Region, Russia, Laboratory of Carbohydrates and Biocides, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Laboratory of Molecular Bioengineering, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: periodate oxidation, EIA, chemical synthesis, MALDI-TOF MS, statistical analysis, immunization, HR-ESI-MS, opsonization assay
- Article ID: 6411
Kasimova AA, Sharar NS, Ambrose SJ, Knirel YA, Shneider MM, Timoshina OY, Popova AV, Perepelov AV, Dmitrenok AS, Hsu LY, Hall RM, Kenyon JJ "The Acinetobacter baumannii K70 and K9 capsular polysaccharides consist of related K-units linked by the same Wzy polymerase and cleaved by the same phage depolymerases" -
Microbiology Spectrum 11(6) (2023) e0302523
Bacteriophage show promise for the treatment of Acinetobacter baumannii infections that resist all therapeutically suitable antibiotics. Many tail-spike depolymerases encoded by phage that are able to degrade A. baumannii capsular polysaccharide (CPS) exhibit specificity for the linkage present between K-units that make up CPS polymers. This linkage is formed by a specific Wzy polymerase, and the ability to predict this linkage using sequence-based methods that identify the Wzy at the K locus could assist with the selection of phage for therapy. However, little is known about the specificity of Wzy polymerase enzymes. Here, we describe a Wzy polymerase that can accommodate two different but similar sugars as one of the residues it links and phage depolymerases that can cleave both types of bond that Wzy forms.
Acinetobacter baumannii, capsular polysaccharide, Wzy polymerase, phage depolymerase, K70
NCBI PubMed ID: 37975684Publication DOI: 10.1128/spectrum.03025-23Journal NLM ID: 101634614Publisher: Washington, DC: ASM Press
Correspondence: J.J. Kenyon
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, Russia, M. M. Shemyakin and Y. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, Centre for Immunology and Infection Control, School of Biomedical Sciences, Faculty of Health, Queensland University of Technology, Brisbane, Australia, School of Life and Environmental Sciences, Faculty of Science, University of Sydney, Sydney, Australia, Saw Swee Hock School of Public Health, National University of Singapore, Queenstown, Singapore, Yong Loo Lin School of Medicine, National University of Singapore, Queenstown, Singapore
Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, sugar analysis, DNA techniques, GLC, Smith degradation, HPLC, GPC, bioinformatic analysis, phage depolymerisation, HR-ESI-MS
- Article ID: 6447
Rai D, Kulkarni SS "Total Synthesis of Conjugation-Ready Tetrasaccharide Repeating Units of a Multidrug-Resistant Pathogen Acinetobacter baumannii Strain 34 and O5" -
Organic Letters 25(46) (2023) 8332-8337
Herein, we report the first total synthesis of conjugation-ready tetrasaccharide repeating units of Acinetobacter baumannii strain 34 and O5 comprising a common disaccharide motif [α-L-FucpNAc-(1→4)-α-D-GalpNAcA]. The installation of 1,2-cis linkages employing a disarmed 2-azido-D-galacturonic acid derivative as the donor is addressed here. The synthesis of the tetrasaccharide repeating units of A. baumannii strain 34 and O5 is accomplished via the longest linear sequences of 19 steps in 9.8% and 21 steps in 8.4% overall yields, respectively.
repeating unit, Acinetobacter baumannii, capsular polysaccharide, O-polysaccharide, total synthesis, A.baumannii 34, A.baumannii O5
NCBI PubMed ID: 37955403Publication DOI: 10.1021/acs.orglett.3c03417Journal NLM ID: 100890393Publisher: American Chemical Society
Correspondence: S.S. Kulkarni
Institutions: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, FTIR, glycosylation, optical rotation measurement, CC, HR-ESI-MS
- Article ID: 6475
Timoshina OY, Kasimova AA, Shneider MM, Matyuta IO, Nikolaeva AY, Evseev PV, Arbatsky NP, Shashkov AS, Chizhov AO, Shelenkov AA, Mikhailova YV, Slukin PV, Volozhantsev NV, Boyko KM, Knirel YA, Miroshnikov KA, Popova AV "Friunavirus Phage-Encoded Depolymerases Specific to Different Capsular Types of Acinetobacter baumannii" -
International Journal of Molecular Sciences 24(10) (2023) 9100
Acinetobacter baumannii is a critical priority nosocomial pathogen that produces a variety of capsular polysaccharides (CPSs), the primary receptors for specific depolymerase-carrying phages. In this study, the tailspike depolymerases (TSDs) encoded in genomes of six novel Friunaviruses, APK09, APK14, APK16, APK86, APK127v, APK128, and one previously described Friunavirus phage, APK37.1, were characterized. For all TSDs, the mechanism of specific cleavage of corresponding A. baumannii capsular polysaccharides (CPSs) was established. The structures of oligosaccharide fragments derived from K9, K14, K16, K37/K3-v1, K86, K127, and K128 CPSs degradation by the recombinant depolymerases have been determined. The crystal structures of three of the studied TSDs were obtained. A significant reduction in mortality of Galleria mellonella larvae infected with A. baumannii of K9 capsular type was shown in the example of recombinant TSD APK09_gp48. The data obtained will provide a better understanding of the interaction of phage-bacterial host systems and will contribute to the formation of principles of rational usage of lytic phages and phage-derived enzymes as antibacterial agents.
Acinetobacter baumannii, capsular polysaccharide, crystal structure, bacteriophage, glycosidase, capsular type, tailspike depolymerase
NCBI PubMed ID: 37240444Publication DOI: 10.3390/ijms24109100Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: A.V. Popova
Institutions: Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 117997 Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, 142279 Obolensk, Russia, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russia, Bach Institute of Biochemistry, Research Centre of Biotechnology of the Russian Academy of Sciences, 119071 Moscow, Russia, Center for Photonics and 2D Materials, Moscow Institute of Physics and Technology, 141700 Dolgoprudny, Russia, Complex of NBICS Technologies, National Research Center 'Kurchatov Institute', 123182 Moscow, Russia, Central Scientific Research Institute of Epidemiology, 111123 Moscow, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, PCR, X-ray, DNA techniques, GPC, enzymatic depolymerization, crystallization, HR-ESI-MS, phage isolation, phage genome analysis, phage propagation, phage sequencing
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