Found 568 structures.
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1. Compound ID: 346
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3HOMyr-(1-2)-+
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Pam-(1-3)-3HOMyr-(1-3)-+ |
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?%Arap4N-(1--P--4)--+ | |
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Pam-(1-3)-3HOMyr-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN
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3HOMyr-(1-3)-+ |
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?%Araf-(1--P--1)--+ |
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Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_136907,IEDB_137340,IEDB_141181,IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 98
Therisod H, Karibian D, Perry MB, Caroff M "Structural analysis of Yersinia pseudotuberculosis ATCC 29833 lipid A" -
International Journal of Mass Spectrometry 219(3) (2002) 549-557
The Yersinia genus includes human and animal pathogens (plague, enterocolitis) as well as non-pathogens. The lipopolysaccharide of the facultative pathogen Yersinia pseudotuberculosis has been implicated in the invasiveness of these bacteria. In this work, we have investigated the fine structure of the lipid A isolated from Y. pseudotuberculosis lipopolysaccharide using chemical analyses, gas chromatography/mass spectrometry, plasma desorption mass spectrometry, and matrix-assisted laser desorption mass spectrometry. Arabinose (Ara) and aminoarabinose (Ara-4N) esterified the phosphates as in Yersinia pestis lipid A. The acylation of Y. pseudotuberculosis lipid A differed from those found in Yersinia enterocolitica, Yersinia ruckeri, and Y. pestis lipopolysaccharides (LPSs): in the distribution of fatty acids between the two glucosamines in the fully acylated hexaacyl molecular species and by the acyloxyacyl substitution at position C-2′, where the Y. pseudotuberculosis lipid A has a C14OC16 making it closest to that of Y. pestis.
lipid A, endotoxin, Yersinia pseudotuberculosis, Y. pseudotuberculosis, PDMS, MALDI
Publication DOI: 10.1016/S1387-3806(02)00706-6Journal NLM ID: 101137096Publisher: Elsevier
Correspondence: martine.caroff@bbmpc.u-psud.fr
Institutions: Equipe “Endotoxines”, UMR 8619 du CNRS, I.B.B.M.C., Université de Paris-Sud, F-Orsay, France, Institute for Biological Sciences, NRC, Ottawa, Ont., Canada
Methods: GC-MS, SDS-PAGE, TLC, ESI-MS, GC, MALDI-TOF MS, composition analysis, mild alkaline degradation, PD-MS
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2. Compound ID: 347
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3HOMyr-(1-3)-+
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?%Ara-(1--P--1)--+ |
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Lau-(1-3)-3HOMyr-(1-3)-+ | |
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C16={11}-(1-3)-3HOMyr-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN
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?%Arap4N-(1--P--4)--+ 3HOMyr-(1-2)-+ |
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Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_136907,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_534864,IEDB_581506
The structure is contained in the following publication(s):
- Article ID: 98
Therisod H, Karibian D, Perry MB, Caroff M "Structural analysis of Yersinia pseudotuberculosis ATCC 29833 lipid A" -
International Journal of Mass Spectrometry 219(3) (2002) 549-557
The Yersinia genus includes human and animal pathogens (plague, enterocolitis) as well as non-pathogens. The lipopolysaccharide of the facultative pathogen Yersinia pseudotuberculosis has been implicated in the invasiveness of these bacteria. In this work, we have investigated the fine structure of the lipid A isolated from Y. pseudotuberculosis lipopolysaccharide using chemical analyses, gas chromatography/mass spectrometry, plasma desorption mass spectrometry, and matrix-assisted laser desorption mass spectrometry. Arabinose (Ara) and aminoarabinose (Ara-4N) esterified the phosphates as in Yersinia pestis lipid A. The acylation of Y. pseudotuberculosis lipid A differed from those found in Yersinia enterocolitica, Yersinia ruckeri, and Y. pestis lipopolysaccharides (LPSs): in the distribution of fatty acids between the two glucosamines in the fully acylated hexaacyl molecular species and by the acyloxyacyl substitution at position C-2′, where the Y. pseudotuberculosis lipid A has a C14OC16 making it closest to that of Y. pestis.
lipid A, endotoxin, Yersinia pseudotuberculosis, Y. pseudotuberculosis, PDMS, MALDI
Publication DOI: 10.1016/S1387-3806(02)00706-6Journal NLM ID: 101137096Publisher: Elsevier
Correspondence: martine.caroff@bbmpc.u-psud.fr
Institutions: Equipe “Endotoxines”, UMR 8619 du CNRS, I.B.B.M.C., Université de Paris-Sud, F-Orsay, France, Institute for Biological Sciences, NRC, Ottawa, Ont., Canada
Methods: GC-MS, SDS-PAGE, TLC, ESI-MS, GC, MALDI-TOF MS, composition analysis, mild alkaline degradation, PD-MS
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3. Compound ID: 1742
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a-D-Manp-(1-2)-+
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a-L-Araf-(1-2)-a-D-Manp-(1-2)-+ |
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-6)-a-D-Manp-(1-6)-a-D-Manp-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: lipoarabiomannan
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_136907,IEDB_140116,IEDB_141793,IEDB_141828,IEDB_141829,IEDB_141831,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_857732,IEDB_857735,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 537
Ma Z, Zhang J, Kong F "Facile synthesis of arabinomannose penta- and decasaccharide fragments of the lipoarabinomannan of the equine pathogen, Rhodococcus equi" -
Carbohydrate Research 339(10) (2004) 1761-1771
Pentasaccharide repeating unit 20 of the lipoarabinomannan from the equine pathogen, Rhodococcus equi, and its dimer 31, were synthesized. The pentasaccharide was obtained by assembling a benzoylated 2,6-branched mannosyl trisaccharide acceptor 13 with a free hydroxyl group at C-2(') of the mannose residue attached to the core mannose residue by (1 [Formula: see text] 6)-linkage, followed by coupling with 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1 [Formula: see text] 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (18), and by deacylation. Meanwhile, the decamer 31 was obtained by firstly preparing a benzoylated mannose (1 [Formula: see text] 6)-linked tetrasaccharide backbone 26 with 2-, 2'-O-ClAc, and 2(')-, 2?-O-Ac groups, respectively, then by dechloroacetylation and subsequent condensation with perbenzoylated trichloroacetimidate, and then by deacetylation and subsequent coupling with 18, and finally, by deacylation
arabinose, Mannose, Regio- and stereoselective synthesis
NCBI PubMed ID: 15220086Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: fzkong@mail.rcees.ac.cn
Institutions: Research Center for Eco-Environmental Sciences, Academia Sinica, PO Box 2871, Beijing 100085, PR China
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4. Compound ID: 1744
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a-D-Manp-(1-2)-+
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a-L-Araf-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-6)-a-D-Manp-(1-1)-Allyl |
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Structure type: oligomer
Trivial name: repeating unit of lipoarabiomannan
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_136907,IEDB_140116,IEDB_141793,IEDB_141829,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 537
Ma Z, Zhang J, Kong F "Facile synthesis of arabinomannose penta- and decasaccharide fragments of the lipoarabinomannan of the equine pathogen, Rhodococcus equi" -
Carbohydrate Research 339(10) (2004) 1761-1771
Pentasaccharide repeating unit 20 of the lipoarabinomannan from the equine pathogen, Rhodococcus equi, and its dimer 31, were synthesized. The pentasaccharide was obtained by assembling a benzoylated 2,6-branched mannosyl trisaccharide acceptor 13 with a free hydroxyl group at C-2(') of the mannose residue attached to the core mannose residue by (1 [Formula: see text] 6)-linkage, followed by coupling with 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1 [Formula: see text] 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (18), and by deacylation. Meanwhile, the decamer 31 was obtained by firstly preparing a benzoylated mannose (1 [Formula: see text] 6)-linked tetrasaccharide backbone 26 with 2-, 2'-O-ClAc, and 2(')-, 2?-O-Ac groups, respectively, then by dechloroacetylation and subsequent condensation with perbenzoylated trichloroacetimidate, and then by deacetylation and subsequent coupling with 18, and finally, by deacylation
arabinose, Mannose, Regio- and stereoselective synthesis
NCBI PubMed ID: 15220086Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: fzkong@mail.rcees.ac.cn
Institutions: Research Center for Eco-Environmental Sciences, Academia Sinica, PO Box 2871, Beijing 100085, PR China
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5. Compound ID: 1745
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a-D-Manp-(1-2)-+
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a-L-Araf-(1-2)-a-D-Manp-(1-2)-+ |
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a-D-Manp-(1-2)-+ | |
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a-L-Araf-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-1)-Allyl |
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Structure type: oligomer
Trivial name: repeating unit of lipoarabiomannan
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_136907,IEDB_140116,IEDB_141793,IEDB_141828,IEDB_141829,IEDB_141831,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_76933,IEDB_857732,IEDB_857735,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 537
Ma Z, Zhang J, Kong F "Facile synthesis of arabinomannose penta- and decasaccharide fragments of the lipoarabinomannan of the equine pathogen, Rhodococcus equi" -
Carbohydrate Research 339(10) (2004) 1761-1771
Pentasaccharide repeating unit 20 of the lipoarabinomannan from the equine pathogen, Rhodococcus equi, and its dimer 31, were synthesized. The pentasaccharide was obtained by assembling a benzoylated 2,6-branched mannosyl trisaccharide acceptor 13 with a free hydroxyl group at C-2(') of the mannose residue attached to the core mannose residue by (1 [Formula: see text] 6)-linkage, followed by coupling with 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1 [Formula: see text] 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (18), and by deacylation. Meanwhile, the decamer 31 was obtained by firstly preparing a benzoylated mannose (1 [Formula: see text] 6)-linked tetrasaccharide backbone 26 with 2-, 2'-O-ClAc, and 2(')-, 2?-O-Ac groups, respectively, then by dechloroacetylation and subsequent condensation with perbenzoylated trichloroacetimidate, and then by deacetylation and subsequent coupling with 18, and finally, by deacylation
arabinose, Mannose, Regio- and stereoselective synthesis
NCBI PubMed ID: 15220086Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: fzkong@mail.rcees.ac.cn
Institutions: Research Center for Eco-Environmental Sciences, Academia Sinica, PO Box 2871, Beijing 100085, PR China
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6. Compound ID: 2037
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a-D-Manp-(1-2)-+
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a-Araf-(1-2)-a-D-Manp-(1-2)-+ |
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-6)-a-D-Manp-(1-6)-a-D-Manp-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: lipoarabinomannan
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_136907,IEDB_140116,IEDB_141793,IEDB_141828,IEDB_141829,IEDB_141831,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_857732,IEDB_857735,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 636
Garton NJ, Gilleron M, Brando T, Dan HH, Giguere S, Puzo G, Prescott JF, Sutcliffe IC "A novel lipoarabinomannan from the equine pathogen Rhodococcus equi. Structure and effect on macrophage cytokine production" -
Journal of Biological Chemistry 277(35) (2002) 31722-31733
Rhodococcus equi is a major cause of foal morbidity and mortality. We have investigated the presence of lipoglycan in this organism as closely related bacteria, notably Mycobacterium tuberculosis, produce lipoarabinomannans (LAM) that may play multiple roles as virulence determinants. The lipoglycan was structurally characterized by gas chromatography-mass spectrometry following permethylation, capillary electrophoresis after chemical degradation, and (1)H and (31)P and two-dimensional heteronuclear nuclear magnetic resonance studies. Key structural features of the lipoglycan are a linear α-1,6-mannan with side chains containing one 2-linked α-D-Manp residue. This polysaccharidic backbone is linked to a phosphatidylinositol mannosyl anchor. In contrast to mycobacterial LAM, there are no extensive arabinan domains but single terminal α-D-Araf residue capping the 2-linked α-D-Manp. The lipoglycan binds concanavalin A and mannose-binding protein consistent with the presence of t-α-D-Manp residues. We studied the ability of the lipoglycans to induce cytokines from equine macrophages, in comparison to whole cells of R. equi. These data revealed patterns of cytokine mRNA induction that suggest that the lipoglycan is involved in much of the early macrophage cytokine response to R. equi infection. These studies identify a novel LAM variant that may contribute to the pathogenesis of disease caused by R. equi.
lipoarabinomannan, cytokines, macrophages, Rhodococcus equi
NCBI PubMed ID: 12072437Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: iain.sutcliffe@sunderland.ac.uk
Institutions: Institute of Pharmacy, Chemistry and Biomedical Sciences, the University of Sunderland, Sunderland SR2 3SD, United Kingdom, Institut de Pharmacologie et de Biologie Structurale du CNRS, 205 Route de Narbonne, 31077 Toulouse Cedex 4, France, the Department of Pathobiology, University of Guelph, Guelph, Ontario N1G 2W1, Canada, College of Veterinary Medicine, University of Florida, Gainesville, Florida 32610-0136
Methods: NMR-2D, NMR, Western blotting, MALDI-TOF MS, electrophoresis, permethylation, CE, acetolysis
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7. Compound ID: 2124
Structure type: monomer
Contained glycoepitopes: IEDB_136907
The structure is contained in the following publication(s):
- Article ID: 677
Hanniffy OM, Shashkov AS, Moran AP, Prendergast MM, Senchenkova SN, Knirel YA, Savage AV "Chemical structure of a polysaccharide from Campylobacter jejuni 176.83 (serotype O:41) containing only furanose sugars" -
Carbohydrate Research 319(1-4) (1999) 124-132
A neutral polysaccharide was obtained by hot phenol-water extraction of biomass from Campylobacter jejuni 176.83 and subsequently separated from acid-liberated core oligosaccharide of lipopolysaccharide by sequential GPC on Bio-Gel P6 and TSK-40 columns. All sugar components of the trisaccharide repeating unit of the polysaccharide were found to be of the furanose ring form. The major trisaccharide contained β-L-arabinose, 6-deoxy-β-D-altro-heptose (β-D-6d-altHep) and 6-deoxy-β-L-altrose (β-L-6d-Alt), whereas in the minor trisaccharide the β-L-6d-Alt is replaced by its C-5 epimer α-D-Fuc. On the basis of 1H and 13C NMR spectroscopic studies, including 2D ROESY, HMQC and HMQC-TOCSY experiments, the following structures of the repeating units were established: [formula: see text]
Campylobacter jejuni, L-Arabinose, O41 polysaccharide structure, 6-deoxy-D-altro-heptose, 6-Deoxy-L-altrose, D-fucose
NCBI PubMed ID: 10520260Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: angela.savage@nuigalway.ie
Institutions: Department of Microbiology, National University of Ireland, Galway, Ireland, Department of Chemistry, National University of Ireland, Galway, Ireland, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow R- 17913, Russia
Methods: NMR-2D, NMR, acid hydrolysis
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8. Compound ID: 2717
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L-Ala-(1-6)-+
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b-D-GlcpNAc-(1-2)-b-D-GalpA-(1-3)-a-D-GlcpNAc-(1-2)-a-L-Araf-(1-2)-D-Thre-ol |
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Structure type: oligomer
Contained glycoepitopes: IEDB_114709,IEDB_135813,IEDB_136907,IEDB_137340,IEDB_141807,IEDB_151531
The structure is contained in the following publication(s):
- Article ID: 940
Linnerborg M, Wollin R, Widmalm G "Structural studies of the O-antigen polysaccharide from Escherichia coli O167" -
European Journal of Biochemistry 246 (1997) 565-573
The structure of the O-antigenic polysaccharide from Escherichia coli O167:H5 has been investigated. Sugar and methylation analyses, fast-atom-bombardment mass spectrometry and 1H- and 13C NMR spectroscopy were the main methods used. The structure of the repeating unit of the polysaccharide was found to be: [formula in text]. Oligosaccharide derivatives of the polysaccharide were obtained by HF solvolysis and by a Smith degradation. Furthermore, base treatment of the polysaccharide led to a degraded polymeric material. For the methylated polysaccharide the amide linkage between alanine and the galacturonic acid residue was reductively cleaved with LiBD4 in ethanol, to give, among other things, a 3-O-methyl galactose derivative.
Lipopolysaccharide, NMR, LPS, structure, structural, polysaccharide, O-antigen, polysaccharides, O antigen, Escherichia, Escherichia coli, structural studies, galactofuranose, galacturonic acid, amide, L-alanine
NCBI PubMed ID: 9208951Publication DOI: 10.1111/j.1432-1033.1997.00565.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden, Swedish Insitute of Infectious Disease Control (SMI), Stockholm, Sweden
Methods: NMR-2D, methylation, FAB-MS, partial acid hydrolysis, NMR, sugar analysis, Smith degradation
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9. Compound ID: 4189
Structure type: oligomer
Contained glycoepitopes: IEDB_136907,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 1554
Perry MB, MacLean LL, Vinogradov E "Structural characterization of the antigenic capsular polysaccharide and lipopolysaccharide O-chain produced by Actinobacillus pleuropneumoniae serotype 15" -
Biochemistry and Cell Biology 83(1) (2005) 61-69
The specific capsular polysaccharide produced by Actinobacillus pleuropneumoniae serotype 15 was determined to be a high-molecular-mass polymer having [alpha]D + 69 degrees (water) and composed of a linear backbone of phosphate diester linked disaccharide units of 2-acetamido-2-deoxy-D-glucose (D-GlcNAc) and 2-acetamido-2-deoxy-D-galactose (D-GalNAc) residues (1:1). Thirty percent of the D-GalNAc residues were substituted at O-4 by beta-D-galactopyranose (beta-D-Galp) residues. Through the application of chemical and NMR methods, the capsule, which defines the serotype specificity of the bacterium, was found to have the structure [structure: see text]. The O-polysaccharide (O-PS) component of the A. pleuropneumoniae serotype 15 lipopolysaccharide (LPS) was characterized as a linear unbranched polymer of repeating pentasaccharide units composed of D-glucose (2 parts) and D-galactose (3 parts), shown to have the structure [structure: see text]. The O-PS was chemically identical with the O-antigen previously identified in the LPSs produced by A. pleuropneumoniae serotypes 3 and 8.
Lipopolysaccharide, capsule, 2-acetamido-2-deoxy-D-galactose, Actinobacillus pleuropneumoniae, 2-acetamido-2-deoxy-D-glucose, Actinobacillus pleuropneumoniae serotype 15
NCBI PubMed ID: 15746967Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
Correspondence: malcolm.perry@nrc-cnrc.gc.ca
Institutions: Institute for Biological Sciences, National Research Council Canada, Ottawa, ON K1A 0R6, Canada
Methods: methylation, NMR, dephosphorylation, deamination, periodate oxidation
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10. Compound ID: 4415
Structure type: polymer chemical repeating unit
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_136044,IEDB_136907,IEDB_137472,IEDB_141794,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1667
Moody SF "Molecular variation in Leishmania" -
Acta Tropica 53 (1993) 185-204
Journal NLM ID: 0370374Publisher: Elsevier
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11. Compound ID: 4420
Structure type: polymer chemical repeating unit
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_136044,IEDB_136907,IEDB_137472,IEDB_141794,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1667
Moody SF "Molecular variation in Leishmania" -
Acta Tropica 53 (1993) 185-204
Journal NLM ID: 0370374Publisher: Elsevier
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12. Compound ID: 4421
Structure type: oligomer
Aglycon: rest of molecule
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_136044,IEDB_136907,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_190606,IEDB_433717,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 1667
Moody SF "Molecular variation in Leishmania" -
Acta Tropica 53 (1993) 185-204
Journal NLM ID: 0370374Publisher: Elsevier
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13. Compound ID: 4424
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a-L-Araf-(1-2)-b-D-Galp-(1-3)-b-D-Galp-(1-4)-D-Manp-(1--/rest of molecule/ |
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Structure type: oligomer
Aglycon: rest of molecule
Compound class: lipophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_136044,IEDB_136907,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_190606,IEDB_433717,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 1667
Moody SF "Molecular variation in Leishmania" -
Acta Tropica 53 (1993) 185-204
Journal NLM ID: 0370374Publisher: Elsevier
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14. Compound ID: 5017
Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_136105,IEDB_136906,IEDB_136907,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
The structure is contained in the following publication(s):
- Article ID: 1966
Joseleau JP, Lapeyre M, Vignon M, Dutton GGS "Chemical and NMR-spectroscopic investigation of the capsular polysaccharide of Klebsiella serotype K41" -
Carbohydrate Research 67 (1978) 197-212
The structure of the repeating unit of the capsular polysaccharide from Klebsiella type 41 has been investigated by methylation analysis of the original and the carboxyl-reduced polymer, uronic acid degradation, Smith degradation, and graded acid hydrolysis. Proton- and 13C-n.m.r. spectroscopy of the original polysaccharide and of the fragments obtained by various methods confirmed some structural features and allowed determination of the anomeric configuration of the glycosidic linkages. This polysaccharide is shown to have the following heptasaccharide repeating-unit: [structure: see text]. This is the first polysaccharide antigen K of the Klebsiella series found to have seven sugar residues in its repeating unit, and to contain a galactose residue in its furanose form.
Publication DOI: 10.1016/S0008-6215(00)83742-8Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Chemistry, University of British Columbia, Vancouver, British Columbia V6T 1W5 Canada, Centre de Recherches sur les Macromolécules Végétales, C.N.R.S., 53X, 38041 Grenoble cédex France
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, partial acid hydrolysis, sugar analysis, acid hydrolysis, GLC, carboxyl reduction, Smith degradation, paper chromatography, periodate oxidation, optical rotation measurement, uronic acid degradation
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15. Compound ID: 5434
Structure type: oligomer
Contained glycoepitopes: IEDB_114706,IEDB_136907
The structure is contained in the following publication(s):
- Article ID: 2276
Daffé M, McNeil M, Brennan PJ "Major structural features of the cell wall arabinogalactans of Mycobacterium, Rhodococcus, and Nocardia spp." -
Carbohydrate Research 249 (1993) 383-398
The cell wall arabinogalactans of strains of Mycobacterium, Rhodococcus, and Nocardia were per-O-methylated, partially hydrolyzed with acid, and the resulting oligosaccharides were reduced and per-O-ethylated to yield per-O-alkylated oligoglycosyl alditol fragments. Analyses of these fragments by gas chromatography-mass spectrometry and of the intact solubilized polysaccharides by 1H and 13C NMR revealed the major structural features of the different arabinogalactans from representatives of the different genera. All of the mycobacterial products contained a homogalactan segment of alternating 5-linked α-Galactofuranosyl (Galf) and 6-linked β-Galf residues. The arabinan segment consisted of three major domains, linear 5-linked α-arabinofuranosyl (Araf) residues and branched (3→5)-linked Araf units substituted with either 5-linked Araf or the disaccharide β-Araf-(1→2)-α-Araf at both branched positions. The recognition of these features in in vivo grown Mycobacterium leprae is an important development. The arabinan from strains of Nocardia contains a nonreducing-end motif composed of the linear trisaccharide, β-Araf-(1→2)-α-Araf-(1→5)-Araf, attached to linear 5-linked α-Araf units. The galactan segment of the arabinogalactan of Nocardia sp. is composed of linear 5-linked β-Galf units substituted in part at O-6 with terminal β-glucosyl units. The two representative strains of Rhodococcus also differed in the composition of the galactan moiety; in addition to the 5-linked Galf, 2- and 3-linked β-Galf units are present. The reducing end of the galactans, and therefore, apparently, of the entire arabinogalactans from all species from all genera, are apparently composed of the unit, rhamnosyl-(1→3)-N-acetyl-glucosamine, which, in turn, is apparently attached to peptidoglycan via phosphodiester linkage.
NCBI PubMed ID: 8275507Publication DOI: 10.1016/0008-6215(93)84102-CJournal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
Methods: 13C NMR, 1H NMR, GLC-MS
- Article ID: 10067
Lau JM, McNeil M, Darvill AG, Albersheim P "Treatment of rhamnogalacturonan I with lithium in ethylenediamine" -
Carbohydrate Research 168 (1987) 245-274
Rhamnogalacturonan I is a pectic polysaccharide that is solubilized from the walls of suspension-cultured sycamore cells (Acer pseudoplatanus) by the action of a highly purified endo-1,4-α-polygalacturonanase. Rhamnogalacturonan I has a linear backbone consisting of the diglycosyl repeating unit, →4)-α-d-GalpA-(1→2)-α-l-Rhap-(1→. Approximately half of the α-l-rhamnosyl residues of the backbone are branched at O-4. Selective cleavage at the galactosyluronic acid residues of the backbone by treatment of rhamnogalacturonan I wit lithium in ethylenediamine resulted in the release of the neutral glycosyl-residue sidechains that had been attached to the backbone. Various analytical techniques, including combined liquid chromatography-mass spectrometry, combined gas-liquid chromatography-mass spectrometry, and 1H-nuclear magnetic resonance spectroscopy, were used to determine the structure of the side chains. The majority of the sidechains were isolated as oligoglycosylalditols, with rhamnitol at the “reducing” end. Terminal 2-, 4-, or 6-linked galactosyl residues were found attached to O-4 of the rhamnitol residues The 2-, 4-, and 6-linked galactosyl residues had terminal or 2-linked arabinosyl, or additional galactosyl, residues attached to them. Based on the results of fast-atom-bombardment mass spectrometry, the side chains were found to range in size from one to fourteen glycosyl residues. The side-chain structures suggest that there are four or more distinct families of side chains attached to the backbone of rhamnogalacturonan I.
Publication DOI: 10.1016/0008-6215(87)80029-0Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Chemistry, University of Colorado, Boulder, and Complex Carbohydrate Research Center and School of Chemical Sciences, University of Georgia, Athens, GA, U.S.A.
Methods: gel filtration, 1H NMR, GLC-MS, FAB-MS
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