Found 9 structures.
Displayed structures from 1 to 9
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1. Compound ID: 4657
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a-Ascp-(1-3)-+ 3,5HOHex-(1-4)-+
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-2)-D-gro-a-D-manHepp-(1-4)-a-L-FucpNAc-(1-3)-b-D-QuipNAc4N-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_2189046
The structure is contained in the following publication(s):
- Article ID: 1778
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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2. Compound ID: 6113
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a-Ascp-(1-3)-+ a-Ascp-(1-3)-+
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a-D-Galp-(1-2)-a-D-Manp-(1-4)-a-L-Rhap-(1-3)-a-D-Galp-(1-2)-a-D-Manp-(1-4)-L-Rha |
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Structure type: oligomer
Contained glycoepitopes: IEDB_130701,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141798,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 2728
Bruse GW, Wollin R, Lindberg AA "Interaction between phage G13 and its oligosaccharide receptor studied by equilibrium dialysis" -
Journal of Molecular Recognition 2 (1989) 18-24
Journal NLM ID: 9004580Publisher: Chichester, Sussex, UK: John Wiley & Sons
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3. Compound ID: 6791
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a-Ascp-(1-3)-+
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a-D-Galp-(1-2)-a-D-Manp-(1-4)-a-L-Rhap-(1--/O(CH2)8COOMe/ |
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Structure type: oligomer
Aglycon: O(CH2)8COOMe
Contained glycoepitopes: IEDB_130701,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 2030
Bock K, Meldal M, Bundle DR, Iversen T, Pinto BM, Garegg PJ, Kvanström I, Norberg T, Lindberg AA, Svenson SB "The conformation of Salmonella O-antigenic oligosaccharides of serogroups A, B, and D1 inferred from 1H- and 13C-nuclear magnetic resonance spectroscopy" -
Carbohydrate Research 130 (1984) 35-53
The conformational model derived by the HSEA calculation method was used to interpret the n.m.r. data for solutions of oligosaccharides corresponding to the Salmonella serogroups A, B, and D1 antigenic determinants. The favored conformer, derived by calculation, accounted for the observed, chemical-shift changes and accurately predicted the existence and magnitude of inter-ring proton n.O.e.'s. Extensive proton-density and compression of proton, Van der Waals radii were correlated with deshielding of specific proton-resonances. The model of lipopolysaccharide conformation accounts for the known antigenic properties of Salmonella O-antigens.
NCBI PubMed ID: 6478461Publication DOI: 10.1016/0008-6215(84)85268-4Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, Stockholm, Sweden, Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario K1A OR6 Canada, Department of Bacteriology, National Bacteriological Laboratory, S-105 21 Stockholm, Sweden, Department of Organic Chemistry, The Technical University of Denmark, 2800 Lyngby Denmark
Methods: 13C NMR, 1H NMR, conformation analysis, nOe, HSEA
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4. Compound ID: 10046
Structure type: monomer
Trivial name: ascarylose
The structure is contained in the following publication(s):
- Article ID: 4176
Thorson JS, Lo SF, Liu HW "Molecular basis of 3,6-dideoxyhexose biosynthesis: Elucidation of CDP-ascarylose biosynthetic genes and their relationship to other 3,6- dideoxyhexose pathways" -
Journal of the American Chemical Society 115 (1993) 5827-5828
Journal NLM ID: 7503056Publisher: American Chemical Society
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5. Compound ID: 11299
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S,S-3,5HOHex-(1-4)-+ a-Ascp-(1-3)-+
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-4)-a-L-FucpNAc-(1-3)-b-D-QuipNAc4N-(1-2)-D-gro-a-D-manHepp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_2189046
The structure is contained in the following publication(s):
- Article ID: 4554
Kokoulin MS, Kalinovsky AI, Komandrova NA, Tovarchi VE, Tomshich SV, Nedashkovskaya OI, Vaskovsky VE "The structure of the O-specific polysaccharide from marine bacterium Litorimonas taeanensis G5 containing 2-acetamido-4-((3S,5S)-3,5-dihydroxyhexanamido)-2,4-dideoxy-D-quinovose and 2-acetamido-2,6-dideoxy-L-xylo-hexos-4-ulose" -
Carbohydrate Research 375 (2013) 105-111
The O-polysaccharide was isolated from the lipopolysaccharide of Litorimonas taeanensis G5T and studied by chemical methods along with 1H and 13C NMR spectroscopy, including 1H, 1H COSY, 1D and 2D TOCSY, NOESY, 1H, 13C HSQC, HMBC, and H2BC experiments. The following new structure of the O-polysaccharide of L. taeanensis G5T containing 2-acetamido-2-deoxy-d-galacturonic acid (d-GalNAcA), 2-acetamido-4-((3S,5S)-3,5-dihydroxyhexanamido)-2,4-dideoxy-d-quinovose (d-QuiNAc4NR), and 2-acetamido-2,6-dideoxy-l-xylo-hexos-4-ulose (l-Sug) was established: where R is (3S,5S)-3,5-dihydroxyhexanoic acid.
O-specific polysaccharide, 2-acetamido-2, 6-dideoxy-L-xylo-hexos-4-ulose, 2-Acetamido-4-((3S, 5S)-3, 5-dihydroxyhexanamido)-2, 4-dideoxy-D-quinovose, Litorimonas taeanensis
NCBI PubMed ID: 23694711Publication DOI: 10.1016/j.carres.2013.04.004Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: maxchem@mail.ru
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, sugar analysis, GLC, mild acid hydrolysis, NMR-1D, triflic acid solvolysis, borohydride reduction
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6. Compound ID: 11969
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?%a-Ascp-(1-4)-a-D-GlcpA-(1-4)-+
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-6)-b-D-GlcpN3(60%)Ac-(1-4)-b-D-GlcpA-(1-3)-b-D-GalpNAc-(1-
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L-Ala-(1-2)-+
Asc = 3,6-dideoxy-L-arabino-hexose (ascarylose) |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_137473,IEDB_140630,IEDB_141807,IEDB_151531,IEDB_153510,IEDB_423153
The structure is contained in the following publication(s):
- Article ID: 4780
Ovchinnikova OG, Moryl M, Shashkov AS, Chizhov AO, Arbatsky NP, Shpirt AM, Rozalski A, Knirel YA "Structure of the O-polysaccharide of Providencia alcalifaciens O2 containing ascarylose and N-(L-alanyl)-D-glucosamine" -
Carbohydrate Research 401 (2015) 11-15
The O-polysaccharide was obtained by degradation of the lipopolysaccharide of Providencia alcalifaciens O2 under mild acidic conditions followed by GPC. The polysaccharide was found to contain two unusual components: 3,6-dideoxy-L-arabino-hexose (ascarylose, Asc) and 2-(L-alanyl)amino-2-deoxy-D-glucose (GlcNAla). Ascarylose was partially split off during lipopolysaccharide degradation and could be eliminated completely by selective acid hydrolysis, which also partially cleaved the β-GAlNAc-(1→6) linkage. The following structure of the branched pentasaccharide repeating unit was established by (1)H and (13)C NMR spectroscopy of the O-polysaccharide and O-deacetylated polysaccharide, as well as products of partial acid hydrolysis: α-Ascp-(1→4)-α-D-GlcpA-(1→4)→6)-β-D-GlcpNAla-(1→4)-β-D-GlpA-(1→3)-β-D-GalpNAc-(1→ ~60% OAc--3).
Lipopolysaccharide, O-antigen, Providencia alcalifaciens, bacterial polysaccharide structure, Ascarylose
NCBI PubMed ID: 25464076Publication DOI: 10.1016/j.carres.2014.10.016Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: yknirel@gmail.com (Y.A. Knirel)
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Immunobiology of Bacteria, Institute of Microbiology, Biotechnology and Immunology, University of Łódź, PL 90-237 Łódź, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, partial acid hydrolysis, ESI-MS, GLC, de-O-acetylation, composition analysis, methanolysis, GPC, mild acid degradation
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7. Compound ID: 11970
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?%a-Ascp-(1-4)-a-D-GlcpA-(1-4)-+
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-6)-b-D-GlcpN-(1-4)-b-D-GlcpA-(1-3)-b-D-GalpNAc-(1-
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L-Ala-(1-2)-+
Asc = 3,6-dideoxy-L-arabino-hexose (ascarylose) |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_137473,IEDB_140630,IEDB_141807,IEDB_151531,IEDB_153510,IEDB_423153
The structure is contained in the following publication(s):
- Article ID: 4780
Ovchinnikova OG, Moryl M, Shashkov AS, Chizhov AO, Arbatsky NP, Shpirt AM, Rozalski A, Knirel YA "Structure of the O-polysaccharide of Providencia alcalifaciens O2 containing ascarylose and N-(L-alanyl)-D-glucosamine" -
Carbohydrate Research 401 (2015) 11-15
The O-polysaccharide was obtained by degradation of the lipopolysaccharide of Providencia alcalifaciens O2 under mild acidic conditions followed by GPC. The polysaccharide was found to contain two unusual components: 3,6-dideoxy-L-arabino-hexose (ascarylose, Asc) and 2-(L-alanyl)amino-2-deoxy-D-glucose (GlcNAla). Ascarylose was partially split off during lipopolysaccharide degradation and could be eliminated completely by selective acid hydrolysis, which also partially cleaved the β-GAlNAc-(1→6) linkage. The following structure of the branched pentasaccharide repeating unit was established by (1)H and (13)C NMR spectroscopy of the O-polysaccharide and O-deacetylated polysaccharide, as well as products of partial acid hydrolysis: α-Ascp-(1→4)-α-D-GlcpA-(1→4)→6)-β-D-GlcpNAla-(1→4)-β-D-GlpA-(1→3)-β-D-GalpNAc-(1→ ~60% OAc--3).
Lipopolysaccharide, O-antigen, Providencia alcalifaciens, bacterial polysaccharide structure, Ascarylose
NCBI PubMed ID: 25464076Publication DOI: 10.1016/j.carres.2014.10.016Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: yknirel@gmail.com (Y.A. Knirel)
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Immunobiology of Bacteria, Institute of Microbiology, Biotechnology and Immunology, University of Łódź, PL 90-237 Łódź, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, partial acid hydrolysis, ESI-MS, GLC, de-O-acetylation, composition analysis, methanolysis, GPC, mild acid degradation
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8. Compound ID: 15764
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a-Ascp-(1-3)-+
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-2)-a-L-Fucp-(1-3)-a-D-Manp-(1-4)-a-L-Fucp-(1-3)-a-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_130701,IEDB_136045,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_152206,IEDB_152214,IEDB_174333,IEDB_885822,IEDB_983930,SB_44,SB_67,SB_72,SB_86
The structure is contained in the following publication(s):
- Article ID: 6089
Knirel YA, Anisimov AP, Kislichkina AA, Kondakova AN, Bystrova OV, Vagaiskaya AS, Shatalin KY, Shashkov AS, Dentovskaya SV "Lipopolysaccharide of the Yersinia pseudotuberculosis Complex" -
Biomolecules 11(10) (2021) 1410
Lipopolysaccharide (LPS), localized in the outer leaflet of the outer membrane, serves as the major surface component of the Gram-negative bacterial cell envelope responsible for the activation of the host's innate immune system. Variations of the LPS structure utilized by Gram-negative bacteria promote survival by providing resistance to components of the innate immune system and preventing recognition by TLR4. This review summarizes studies of the biosynthesis of Yersinia pseudotuberculosis complex LPSs, and the roles of their structural components in molecular mechanisms of yersiniae pathogenesis and immunogenesis.
core, Pathogenesis, lipid A, Yersinia pseudotuberculosis, lipopolysaccharide (LPS), Yersinia pestis, Plague, pathogenicity factor
NCBI PubMed ID: 34680043Publication DOI: 10.3390/biom11101410Journal NLM ID: 101596414Publisher: Basel, Switzerland: MDPI
Correspondence: Y.A. Knirel
; S.V. Dentovskaya
Institutions: Laboratory of Carbohydrate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Laboratory for Plague Microbiology, Especially Dangerous Infections Department, State Research Center for Applied Microbiology and Biotechnology, 142279 Obolensk, Russia, Department of Biochemistry and Molecular Pharmacology, New York University School of Medicine, New York, NY 10016, USA
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9. Compound ID: 16254
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a-Ascp-(1-4)-a-D-GlcpA-(1-4)-+
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-6)-b-D-GlcpN-(1-4)-b-D-GlcpA-(1-3)-b-D-GalpNAc-(1-
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L-Ala-(1-2)-+ |
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Structure type: polymer chemical repeating unit
Compound class: O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_137473,IEDB_140630,IEDB_141807,IEDB_151531,IEDB_153510,IEDB_423153
The structure is contained in the following publication(s):
- 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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