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1. Compound ID: 17
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a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-+
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a-D-GlcpNAc-(1-2)-+ |
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EtN-(1--P--3)--L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Trivial name: lipooligosaccharide core L1
Compound class: core oligosaccharide, LOS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152217,IEDB_190606,IEDB_2189047,IEDB_418765,IEDB_418766,IEDB_418767,IEDB_418768,IEDB_418769,IEDB_418770,IEDB_419428,IEDB_419429,IEDB_423106,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 7
Berrington AW, Tan YC, Srikhanta Y, Kuipers B, van der LP, Peak IR, Jennings MP "Phase variation in meningococcal lipooligosaccharide biosynthesis genes" -
FEMS Immunology and Medical Microbiology 34(4) (2002) 267-275
Neisseria meningitidis expresses a range of lipooligosaccharide (LOS) structures, comprising of at least 13 immunotypes (ITs). Meningococcal LOS is subject to phase variation of its terminal structures allowing switching between ITs, which is proposed to have functional significance in disease. The objectives of this study were to investigate the repertoire of structures that can be expressed in clinical isolates, and to examine the role of phase-variable expression of LOS genes during invasive disease. Southern blotting was used to detect the presence of LOS biosynthetic genes in two collections of meningococci, a global set of strains previously assigned to lineages of greater or lesser virulence, and a collection of local clinical isolates which included paired throat and blood isolates from individual patients. Where the phase-variable genes lgtA, lgtC or lgtG were identified, they were amplified by PCR and the homopolymeric tracts, responsible for their phase-variable expression, were sequenced. The results revealed great potential for variation between alternate LOS structures in the isolates studied, with most strains capable of expressing several alternative terminal structures. The structures predicted to be currently expressed by the genotype of the strains agreed well with conventional immunotyping. No correlation was observed between the structural repertoire and virulence of the isolate. Based on the potential for LOS phase variation in the clinical collection and observations with the paired patient isolates, our data suggest that phase variation of LOS structures is not required for translocation between distinct compartments in the host
Lipopolysaccharide, biosynthesis, structure, Meningococcus, Phase variation, Lipooligosaccharide, Pathogenesis, Neisseria meningitidis, alternative, Bacterial Proteins, biosynthetic, blood, blotting, chemistry, clinical, correlation, disease, expression, functional, gene, Gene Expression Regulation, Bacterial, genetics, genotype, growth & development, host, human, immunotype, immunotyping, invasive, isolate, LOS, meningococcal, Meningococcal Infections, meningococci, metabolism, microbiology, Neisseria, pathogenicity, PCR, phase, phenotype, polymerase chain reaction, potential, role, Sequence Analysis, DNA, significance, strain, structural, Support, Non-U.S.Gov't, terminal, tract, translocation, variation, Variation (Genetics), virulence
NCBI PubMed ID: 12443826Journal NLM ID: 9315554Publisher: Elsevier
Correspondence: jennings@biosci.uq.edu.au
Institutions: Department of Microbiology and Parasitology, University of Queensland, St. Lucia, Brisbane, Qld 4072, Australia, National Institute of Public Health and the Environment, Bilthoven, The Netherlands, School of Health Science, Gri?th University, Gold Coast Campus, Qld 4217, Australia
Methods: PCR, DNA sequencing
- Article ID: 1621
Kahler CM, Datta A, Tzeng YL, Carlson RW, Stephens DS "Inner core assembly and structure of the lipooligosaccharide of Neisseria meningitidis: capacity of strain NMB to express all known immunotype epitopes" -
Glycobiology 15(4) (2005) 409-419
Neisseria meningitidis expresses a heterogeneous population of lipooligosaccharide (LOS) inner cores variously substituted with α1-3-linked glucose and O-3, O-6, and O-7 linked phosphoethanolamine (PEA), as well as glycine, attached to HepII. Combinations of these attachments to the LOS inner core represent immunodominant epitopes that are being exploited as future vaccine candidates. Historically, each LOS immunotype was structurally assessed and prescribed a certain unique inner core epitope. We report that a single isolate, strain NMB, possesses the capacity to produce all of the known neisserial LOS inner core immunotype structures. Analysis of the inner cores from parental LOS revealed the presence or absence of α1,3-linked glucose, O-6 and/or O-7 linked PEA, in addition to glycine attached at the 7 position of the HepII inner core. Identification and inactivation of lpt-6 in strain NMB resulted in the loss of both O-6 and O-7 linked PEA groups from the LOS inner core, suggesting that Lpt-6 of strain NMB may have bifunctional transferase activities or that the O-6 linked PEA groups once attached to the inner core undergo nonenzymatic transfer to the O-7 position of HepII. Although O-3 linked PEA was not detected in parental LOS inner cores devoid of α1-3-linked glucose residues, LOS glycoforms bearing O-3 PEA groups accumulated in a truncated mutant, NMBlgtK (Hep2Kdo2-lipid A). Because these structures disappeared upon inactivation of the lpt-3 locus, strain NMB expresses a functional O-3 PEA transferase. The LOS glycoforms expressed by NMBlgtK were also devoid of glycine attachments, indicating that glycine was added to the inner core after the completion of the gamma-chain by LgtK. In conclusion, strain NMB has the capability to express all known inner core structures, but in in vitro culture L2 and L4 immunotype structures are predominantly expressed.
NMR, structure, core, Lipooligosaccharide, Neisseria meningitidis, immunotype, PCR, epitopes, mass spectrometry, inner core, MALDI-TOF, phosphoethanolamine, MS, vaccine, GLC, matrix-assisted laser desorption ionization time of flight, MDO, membrane-derived oligosaccharide, gas-liquid chromatography, heptose PEA transferase, PMAA, partially methylated/ethylated aldtitol acetate
NCBI PubMed ID: 15574803Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: charlene.kahler@med.monoash.edu.au
Institutions: Department of Microbiology, Monash University, Clayton 3800, Australia
Methods: methylation, NMR, sugar analysis, MALDI-TOF MS
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2. Compound ID: 66
Structure type: oligomer
Trivial name: globotriose
Contained glycoepitopes: IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_1391964,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152217,IEDB_190606,IEDB_423106,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 16
Blixt O, Van Die I, Norberg T, van den Eijnden DH "High-level expression of the Neisseria meningitidis lgtA gene in Escherichia coli and characterization of the encoded N-acetylglucosaminyltransferase as a useful catalyst in the synthesis of GlcNAcb1→3Gal and GalNAcb1-3Gal linkages" -
Glycobiology 9(10) (1999) 1061-1071
We have expressed the Neisseria meningitidis lgtA gene at a high level in Escherichia coli. The encoded β-N-acetylglucosaminyltransferase, referred to as LgtA, which in the bacterium is involved in the synthesis of the lacto-N-neo-tetraose structural element of the bacterial lipooligosaccharide, was obtained in an enzymatically highly active form. This glycosyltransferase appeared to be unusual in that it displays a broad acceptor specificity toward both α- and β-galactosides, whether structurally related to N- or O-protein-, or lipid-linked oligosaccharides. Product analysis by one- and two-dimensional 400 MHz 1H- and 13C NMR spectroscopy reveals that LgtA catalyzes the introduction of GlcNAc from UDP-GlcNAc in a β1→3-linkage to accepting Gal residues. The enzyme can thus be characterized as a UDP-GlcNAc:Gal α/β-R β 3-N-acetylglucosaminyltransferase. Although lactose is a highly preferred acceptor substrate the recombinant enzyme also acts efficiently on monomeric and dimeric N-acetyllactosamine revealing its potential value in the synthesis of polylactosaminoglycan structures in enzyme assisted procedures. Furthermore, LgtA shows a high donor promiscuity toward UDP-GalNAc, but not toward other UDP-sugars, and can catalyze the introduction of GalNAc in β1→3-linkage to α- or β-Gal in the acceptor structures at moderate rates. LgtA therefore shows promise to be a useful catalyst in the preparative synthesis of both GlcNAc β1→3 Gal and GalNAc β1→3 Gal linkages.
oligosaccharide, enzyme-assisted-synthesis, recombinant glycosyltransferase, glycosidic linkage, polylactosaminoglycan, recombinant glycosyltrasferase
NCBI PubMed ID: 10521543Publication DOI: 10.1093/glycob/9.10.1061Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Medical Chemistry, Vrije Universiteit, Van der Boechorstraat 7, 1081 BT Amsterdam, The Netherlands
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, enzyme-assisted synthesis, DNA techniques, glycosyltransferase assays, kinetics assays
- Article ID: 701
Johnson KF "Synthesis of oligosaccharides by bacterial enzymes" -
Glycoconjugate Journal 16(2) (1999) 141-146
Many human pathogens initiate disease by utilizing their microbial adhesin proteins to attach to glycoconjugates on host cell mucosal surfaces. Soluble oligosaccharides of identical or similar structure to these naturally occurring ligands can both prevent bacterial attachment as well as mediate the release of attached bacteria. Since it has not been possible to isolate large quantities of these compounds, we have developed enzyme-based technologies to synthesize several relevant human oligosaccharides. Using cloned bacterial glycosyltransferases, we can synthesize several hundred grams of these oligosaccharides at a time. The availability of these large quantities will allow these compounds to be tested as anti-adhesive pharmaceutical agents as well as lead to expanded practical applications.
synthesis, oligosaccharide, Bacterial, Oligosaccharides, enzyme, glycosyltransferase, Enzymes
NCBI PubMed ID: 10612413Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Correspondence: Kjohnson@neose.com
Institutions: Neose Technologies, Department of Molecular Biology, Horsham, USA, Neose Technologies, epartment of Molecular Biology, Horsham, USA
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3. Compound ID: 204
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b-D-Galp-(1-4)-a-D-GlcpNAc-(1-2)-b-D-Glcp-(1-4)-+
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a-D-Galp-(1-4)-b-D-Galp-(1-4)-a-D-Glcp-(1-2)-b-D-Glcp-(1-6)-a-D-Glcp-(1-5)-Kdo
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b-D-Glcp-(1-3)-+ |
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Structure type: oligomer
Trivial name: glycoform 3
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_140108,IEDB_141794,IEDB_141806,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152217,IEDB_190606,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_178,SB_187,SB_192,SB_195,SB_30,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 50
Edebrink P, Jansson P, Jansson PE, Rahman MM, Widmalm G, Holme T, Rahman M "Structural studies of the O-antigen oligosaccharides from two strains of Moraxella catarrhalis serotype C" -
Carbohydrate Research 266 (1995) 237-261
The oligosaccharide parts from Moraxella (Branhamella) catarrhalis serotype C lipooligosaccharides were isolated by mild acid hydrolysis followed by gel permeation chromatography. Four different oligosaccharides could be identified from strain RS26 and two from strain RS10. The structures of the O-oligosaccharides were established by methylation analyses, mass spectrometry, and NMR spectroscopy. It is concluded that the oligosaccharide O-antigens from RS26 are a mixture of octa-, deca-, and undeca-saccharides, and most likely a heptasaccharide. Strain RS10 contains the deca- and the undeca-saccharide only. The structures for the oligosaccharides are shown below. [formula: see text] OS(7) [formula: see text] OS(8) [formula: see text] OS(10) [formula: see text] OS(11) Methylation analysis of the intact lipooligosaccharides showed that two Kdo residues were present, one terminal and one 4,5-substituted residue. It also showed that they consisted of a lipid A portion with 6-substituted glucosamine residues.
NMR, Lipooligosaccharide, Moraxella catarrhalis, Branhamella
NCBI PubMed ID: 7535189Publication DOI: 10.1016/0008-6215(94)00276-LJournal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden
Methods: NMR-2D, methylation, NMR, sugar analysis, MS
- Article ID: 52
Edebrink P, Jansson PE, Widmalm G, Holme T, Rahman M "The structures of oligosaccharides isolated from the lipopolysaccharide of Moraxella catarrhalis serotype B, strain CCUG 3292" -
Carbohydrate Research 295 (1996) 127-146
The oligosaccharides from the lipopolysaccharides of Moraxella catarrhalis serotype B, strain CCUG 3292, were isolated after mild acid hydrolysis and separated by high-performance anion-exchange chromatography. The structures of the oligosaccharides were established by fast atom bombardment mass spectrometry and nuclear magnetic resonance spectroscopy. It is concluded that the oligosaccharides comprise a mixture of mainly a nona- and a deca-saccharide. [formula: see text] Smaller amounts of undeca-saccharides and of truncated forms, namely, hexa-, hepta-, and octa-saccharides, were also detected
Lipopolysaccharide, NMR, Moraxella catarrhalis, Branhamella
NCBI PubMed ID: 9002189Publication DOI: 10.1016/S0008-6215(96)90132-9Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Pererik.Jansson@kfcm13.hs.sll.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden, Clinical Research Centre, Analytical Unit, Karolinska Institute, Huddinge, Sweden, Microbiology and Tumor Biology Center, Division of Bacteriology, Karolinska Institute, Stockholm, Sweden
Methods: NMR-2D, methylation, NMR, sugar analysis, MS
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4. Compound ID: 205
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a-D-Galp-(1-4)-b-D-Galp-(1-4)-a-D-Glcp-(1-2)-b-D-Glcp-(1-6)-+
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a-D-Galp-(1-4)-b-D-Galp-(1-4)-a-D-GlcpNAc-(1-2)-b-D-Glcp-(1-4)-a-D-Glcp-(1-5)-Kdo
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b-D-Glcp-(1-3)-+ |
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Structure type: oligomer
Trivial name: glycoform 4
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_140108,IEDB_141794,IEDB_141806,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144991,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152217,IEDB_190606,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_177,SB_178,SB_187,SB_192,SB_195,SB_30,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 50
Edebrink P, Jansson P, Jansson PE, Rahman MM, Widmalm G, Holme T, Rahman M "Structural studies of the O-antigen oligosaccharides from two strains of Moraxella catarrhalis serotype C" -
Carbohydrate Research 266 (1995) 237-261
The oligosaccharide parts from Moraxella (Branhamella) catarrhalis serotype C lipooligosaccharides were isolated by mild acid hydrolysis followed by gel permeation chromatography. Four different oligosaccharides could be identified from strain RS26 and two from strain RS10. The structures of the O-oligosaccharides were established by methylation analyses, mass spectrometry, and NMR spectroscopy. It is concluded that the oligosaccharide O-antigens from RS26 are a mixture of octa-, deca-, and undeca-saccharides, and most likely a heptasaccharide. Strain RS10 contains the deca- and the undeca-saccharide only. The structures for the oligosaccharides are shown below. [formula: see text] OS(7) [formula: see text] OS(8) [formula: see text] OS(10) [formula: see text] OS(11) Methylation analysis of the intact lipooligosaccharides showed that two Kdo residues were present, one terminal and one 4,5-substituted residue. It also showed that they consisted of a lipid A portion with 6-substituted glucosamine residues.
NMR, Lipooligosaccharide, Moraxella catarrhalis, Branhamella
NCBI PubMed ID: 7535189Publication DOI: 10.1016/0008-6215(94)00276-LJournal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden
Methods: NMR-2D, methylation, NMR, sugar analysis, MS
- Article ID: 52
Edebrink P, Jansson PE, Widmalm G, Holme T, Rahman M "The structures of oligosaccharides isolated from the lipopolysaccharide of Moraxella catarrhalis serotype B, strain CCUG 3292" -
Carbohydrate Research 295 (1996) 127-146
The oligosaccharides from the lipopolysaccharides of Moraxella catarrhalis serotype B, strain CCUG 3292, were isolated after mild acid hydrolysis and separated by high-performance anion-exchange chromatography. The structures of the oligosaccharides were established by fast atom bombardment mass spectrometry and nuclear magnetic resonance spectroscopy. It is concluded that the oligosaccharides comprise a mixture of mainly a nona- and a deca-saccharide. [formula: see text] Smaller amounts of undeca-saccharides and of truncated forms, namely, hexa-, hepta-, and octa-saccharides, were also detected
Lipopolysaccharide, NMR, Moraxella catarrhalis, Branhamella
NCBI PubMed ID: 9002189Publication DOI: 10.1016/S0008-6215(96)90132-9Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Pererik.Jansson@kfcm13.hs.sll.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden, Clinical Research Centre, Analytical Unit, Karolinska Institute, Huddinge, Sweden, Microbiology and Tumor Biology Center, Division of Bacteriology, Karolinska Institute, Stockholm, Sweden
Methods: NMR-2D, methylation, NMR, sugar analysis, MS
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5. Compound ID: 206
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a-D-GlcpNAc-(1-2)-b-D-Glcp-(1-4)-+
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a-D-Galp-(1-4)-b-D-Galp-(1-4)-a-D-Glcp-(1-2)-b-D-Glcp-(1-6)-a-D-Glcp-(1-5)-Kdo
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b-D-Glcp-(1-3)-+ |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141806,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152217,IEDB_190606,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_178,SB_187,SB_192,SB_195,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 50
Edebrink P, Jansson P, Jansson PE, Rahman MM, Widmalm G, Holme T, Rahman M "Structural studies of the O-antigen oligosaccharides from two strains of Moraxella catarrhalis serotype C" -
Carbohydrate Research 266 (1995) 237-261
The oligosaccharide parts from Moraxella (Branhamella) catarrhalis serotype C lipooligosaccharides were isolated by mild acid hydrolysis followed by gel permeation chromatography. Four different oligosaccharides could be identified from strain RS26 and two from strain RS10. The structures of the O-oligosaccharides were established by methylation analyses, mass spectrometry, and NMR spectroscopy. It is concluded that the oligosaccharide O-antigens from RS26 are a mixture of octa-, deca-, and undeca-saccharides, and most likely a heptasaccharide. Strain RS10 contains the deca- and the undeca-saccharide only. The structures for the oligosaccharides are shown below. [formula: see text] OS(7) [formula: see text] OS(8) [formula: see text] OS(10) [formula: see text] OS(11) Methylation analysis of the intact lipooligosaccharides showed that two Kdo residues were present, one terminal and one 4,5-substituted residue. It also showed that they consisted of a lipid A portion with 6-substituted glucosamine residues.
NMR, Lipooligosaccharide, Moraxella catarrhalis, Branhamella
NCBI PubMed ID: 7535189Publication DOI: 10.1016/0008-6215(94)00276-LJournal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden
Methods: NMR-2D, methylation, NMR, sugar analysis, MS
- Article ID: 52
Edebrink P, Jansson PE, Widmalm G, Holme T, Rahman M "The structures of oligosaccharides isolated from the lipopolysaccharide of Moraxella catarrhalis serotype B, strain CCUG 3292" -
Carbohydrate Research 295 (1996) 127-146
The oligosaccharides from the lipopolysaccharides of Moraxella catarrhalis serotype B, strain CCUG 3292, were isolated after mild acid hydrolysis and separated by high-performance anion-exchange chromatography. The structures of the oligosaccharides were established by fast atom bombardment mass spectrometry and nuclear magnetic resonance spectroscopy. It is concluded that the oligosaccharides comprise a mixture of mainly a nona- and a deca-saccharide. [formula: see text] Smaller amounts of undeca-saccharides and of truncated forms, namely, hexa-, hepta-, and octa-saccharides, were also detected
Lipopolysaccharide, NMR, Moraxella catarrhalis, Branhamella
NCBI PubMed ID: 9002189Publication DOI: 10.1016/S0008-6215(96)90132-9Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Pererik.Jansson@kfcm13.hs.sll.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden, Clinical Research Centre, Analytical Unit, Karolinska Institute, Huddinge, Sweden, Microbiology and Tumor Biology Center, Division of Bacteriology, Karolinska Institute, Stockholm, Sweden
Methods: NMR-2D, methylation, NMR, sugar analysis, MS
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6. Compound ID: 210
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b-D-Galp-(1-4)-a-D-Glcp-(1-2)-b-D-Glcp-(1-4)-+
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a-D-Galp-(1-4)-b-D-Galp-(1-4)-a-D-Glcp-(1-2)-b-D-Glcp-(1-6)-a-D-Glcp-(1-5)-Kdo
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b-D-Glcp-(1-3)-+ |
Show graphically |
Structure type: oligomer
Trivial name: glycoform 2
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141806,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152217,IEDB_190606,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_178,SB_187,SB_192,SB_195,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 52
Edebrink P, Jansson PE, Widmalm G, Holme T, Rahman M "The structures of oligosaccharides isolated from the lipopolysaccharide of Moraxella catarrhalis serotype B, strain CCUG 3292" -
Carbohydrate Research 295 (1996) 127-146
The oligosaccharides from the lipopolysaccharides of Moraxella catarrhalis serotype B, strain CCUG 3292, were isolated after mild acid hydrolysis and separated by high-performance anion-exchange chromatography. The structures of the oligosaccharides were established by fast atom bombardment mass spectrometry and nuclear magnetic resonance spectroscopy. It is concluded that the oligosaccharides comprise a mixture of mainly a nona- and a deca-saccharide. [formula: see text] Smaller amounts of undeca-saccharides and of truncated forms, namely, hexa-, hepta-, and octa-saccharides, were also detected
Lipopolysaccharide, NMR, Moraxella catarrhalis, Branhamella
NCBI PubMed ID: 9002189Publication DOI: 10.1016/S0008-6215(96)90132-9Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Pererik.Jansson@kfcm13.hs.sll.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden, Clinical Research Centre, Analytical Unit, Karolinska Institute, Huddinge, Sweden, Microbiology and Tumor Biology Center, Division of Bacteriology, Karolinska Institute, Stockholm, Sweden
Methods: NMR-2D, methylation, NMR, sugar analysis, MS
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7. Compound ID: 214
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a-D-Galp-(1-4)-b-D-Galp-(1-4)-a-D-Glcp-(1-2)-b-D-Glcp-(1-6)-+
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a-D-Galp-(1-4)-b-D-Galp-(1-4)-a-D-Glcp-(1-2)-b-D-Glcp-(1-4)-a-D-Glcp-(1-5)-Kdo
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b-D-Glcp-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141806,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152217,IEDB_190606,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_178,SB_187,SB_192,SB_195,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 52
Edebrink P, Jansson PE, Widmalm G, Holme T, Rahman M "The structures of oligosaccharides isolated from the lipopolysaccharide of Moraxella catarrhalis serotype B, strain CCUG 3292" -
Carbohydrate Research 295 (1996) 127-146
The oligosaccharides from the lipopolysaccharides of Moraxella catarrhalis serotype B, strain CCUG 3292, were isolated after mild acid hydrolysis and separated by high-performance anion-exchange chromatography. The structures of the oligosaccharides were established by fast atom bombardment mass spectrometry and nuclear magnetic resonance spectroscopy. It is concluded that the oligosaccharides comprise a mixture of mainly a nona- and a deca-saccharide. [formula: see text] Smaller amounts of undeca-saccharides and of truncated forms, namely, hexa-, hepta-, and octa-saccharides, were also detected
Lipopolysaccharide, NMR, Moraxella catarrhalis, Branhamella
NCBI PubMed ID: 9002189Publication DOI: 10.1016/S0008-6215(96)90132-9Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Pererik.Jansson@kfcm13.hs.sll.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden, Clinical Research Centre, Analytical Unit, Karolinska Institute, Huddinge, Sweden, Microbiology and Tumor Biology Center, Division of Bacteriology, Karolinska Institute, Stockholm, Sweden
Methods: NMR-2D, methylation, NMR, sugar analysis, MS
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8. Compound ID: 220
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a-Kdop-(2-4)-+
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a-D-GlcpNAc-(1-2)-b-D-Glcp-(1-4)-+ |
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a-D-Galp-(1-4)-b-D-Galp-(1-4)-a-D-Glcp-(1-2)-b-D-Glcp-(1-6)-a-D-Glcp-(1-5)-Kdo
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b-D-Glcp-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130651,IEDB_130659,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141806,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152217,IEDB_190606,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_178,SB_187,SB_192,SB_195,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 55
Ekelöf K, Oscarson S "Synthesis of 2-(4-aminophenyl)ethyl 3-deoxy-5-O-(3,4,6-tri-O-b-D-glucopyranosyl-a-D-glycopyranosyl)-a-D-manno-oct-2-ulo pyranosidonic acid, a highly branched pentasaccharide corresponding to structures found in lipopolysaccharides from Moraxella catarrhalis" -
Carbohydrate Research 278(2) (1995) 289-300
Syntheses of the pentasaccharide 2-(4-aminophenyl)ethyl 3-deoxy-5-O-(3,4,6- tri-O-β-D-glucopyranosyl-α-D-glucopyranosyl)-α-D-manno-oct-2- ulopyranosidonic acid and of the tetrasaccharide 3,4,6-tri-O-β-D-glucopyranosyl-α-D-glucopyranoside, both as its methyl and 2-(4-trifluoro-acetamidophenyl)ethyl glycoside, are described. These oligosaccharides correspond to structures found in the lipopolysaccharide of Moraxella catarrhalis and were needed for biological experiments aimed at producing antibodies against the bacteria. The best way to introduce the glucopyranosyl groups into the 3-, 4-, and 6-positions of the branched target compounds was found to be a one-step reaction using a 3,4,6-triol as acceptor and 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl bromide as donor in a silver trifluoromethanesulfonate-promoted coupling. The spacer arm, necessary for the formation of immunoactive glycoconjugates, was introduced into the glucose moiety via a dimethyl(methylthio)sulfonium trifluoromethanesulfonate-promoted reaction using the ethyl thioglucoside as donor, whereas for Kdo, the acetylated glycal derivative, methyl 4,5,7,8-tetra-O-acetyl-2,6-anhydro-3-deoxy-D-manno-oct-2-enonate, was used as donor and phenylselenyl trifluoromethanesulfonate as a stereocontrolling promoter
carbohydrates, Kdo, glycoconjugates, oligosaccharide synthesis, Bacterial antigens
NCBI PubMed ID: 8590446Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden
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9. Compound ID: 223
|
a-Kdo-(2-4)-+
|
a-D-GlcpNAc-(1-2)-b-D-Glcp-(1-4)-+ |
| |
a-D-Galp-(1-4)-b-D-Galp-(1-4)-a-D-Glcp-(1-2)-b-D-Glcp-(1-6)-a-D-Glcp-(1-5)-Kdo
|
b-D-Glcp-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130651,IEDB_130659,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141806,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152217,IEDB_190606,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_178,SB_187,SB_192,SB_195,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 56
Ekelöf K, Oscarson S "Synthesis of oligosaccharide structures from the lipopolysaccharide of Moraxella catarrhalis" -
Journal of Organic Chemistry 61 (1996) 7711-7718
The synthesis of the octasaccharide [p-(trifluoroacetamido)phenyl]ethyl 4-O-[2-O-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-β-D-glucopyranosyl]-6-O-[2-O-[4-O-(4-O-α-D-galactopyranosyl-β-D-galactopyranosyl)-α-D-glucopyranosyl]-β-D-glucopyranosyl]-3-O-β-D-glucopyranosyl-α-D-glucopyranoside, representing the outer part of the lipooligosaccharide from Moraxella catarrhalis serotype A, is described, together with a hepta-, a hexa-, and a pentasaccaride, composing parts thereof with shorter oligosaccharide chains substituted in the 6-position of the central 3,4,6-branched glucose moiety. The versatility of the use of thioglycosides in oligosaccharide synthesis is shown, since throughout the synthesis thioglycosides are used as glycosyl donor precursors, either directly in dimethyl(methylthio)sulfonium triflate (DMTST)-promoted coupling reactions or after conversion to the corresponding glycosyl bromide in silver triflate-promoted couplings. The effects of different protecting groups, anomeric leaving groups, and solvents used in the various coupling reactions are often substantial, which necessitates the use of easily convertible intermediates
Lipopolysaccharide, synthesis, LPS, oligosaccharide, oligosaccharide structure, structure, core, Moraxella catarrhalis, Moraxella
NCBI PubMed ID: 11667725Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
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10. Compound ID: 226
|
a-D-GlcpNAc-(1-2)-b-D-Glcp-(1-4)-+
|
a-D-Galp-(1-4)-b-D-Galp-(1-4)-a-D-Glcp-(1-2)-b-D-Glcp-(1-6)-a-D-Glcp-(1--/p-(trifluoroacetamido)phenyl]ethyl/
|
b-D-Glcp-(1-3)-+ |
Show graphically |
Structure type: oligomer
Aglycon: p-(trifluoroacetamido)phenyl]ethyl
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141806,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152217,IEDB_190606,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_178,SB_187,SB_192,SB_195,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 56
Ekelöf K, Oscarson S "Synthesis of oligosaccharide structures from the lipopolysaccharide of Moraxella catarrhalis" -
Journal of Organic Chemistry 61 (1996) 7711-7718
The synthesis of the octasaccharide [p-(trifluoroacetamido)phenyl]ethyl 4-O-[2-O-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-β-D-glucopyranosyl]-6-O-[2-O-[4-O-(4-O-α-D-galactopyranosyl-β-D-galactopyranosyl)-α-D-glucopyranosyl]-β-D-glucopyranosyl]-3-O-β-D-glucopyranosyl-α-D-glucopyranoside, representing the outer part of the lipooligosaccharide from Moraxella catarrhalis serotype A, is described, together with a hepta-, a hexa-, and a pentasaccaride, composing parts thereof with shorter oligosaccharide chains substituted in the 6-position of the central 3,4,6-branched glucose moiety. The versatility of the use of thioglycosides in oligosaccharide synthesis is shown, since throughout the synthesis thioglycosides are used as glycosyl donor precursors, either directly in dimethyl(methylthio)sulfonium triflate (DMTST)-promoted coupling reactions or after conversion to the corresponding glycosyl bromide in silver triflate-promoted couplings. The effects of different protecting groups, anomeric leaving groups, and solvents used in the various coupling reactions are often substantial, which necessitates the use of easily convertible intermediates
Lipopolysaccharide, synthesis, LPS, oligosaccharide, oligosaccharide structure, structure, core, Moraxella catarrhalis, Moraxella
NCBI PubMed ID: 11667725Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
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11. Compound ID: 236
|
a-D-GlcpNAc-(1-2)-D-gro-a-D-Hepp-(1-3)-+ a-Kdop-(2-4)-+
| |
a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_130650,IEDB_130651,IEDB_130659,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_1391964,IEDB_140087,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152217,IEDB_190606,IEDB_2189047,IEDB_423106,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 58
Erwin AL, Haynes PA, Rice PA, Gotschlich EC "Conservation of the lipooligosaccharide synthesis locus lgt among strains of Neisseria gonorrhoeae: Requirement for lgtE in synthesis of the 2C7 epitope and of the b chain of strain 15253" -
Journal of Experimental Medicine 184 (1996) 1233-1241
The present study was undertaken to examine the extent to which the lgt locus varies among strains of gonococci. This locus encodes five glycosyl transferases involved in the synthesis of the lipooligosaccharide (LOS) of Neisseria gonorrhoeae. We examined seven gonococcal strains and found that the structure of the lgt locus is conserved among six of these strains. The locus is strikingly altered in strain 15253. This is one of the few strains where extensive structural analysis of its LOS is available, and therefore, we defined the altered lgt locus and focused on the reactivity of mAB 2C7. We found that strain 15253 contains only two lgt genes, lgtA and lgtE. As in F62, lgtA encodes a GlcNAc transferase and is subject to phase variation. In addition, by analysis of deletion mutants, we found that lgtE, which encodes a galactosyl transferase that is required for elongating the alpha-chain, is also necessary for completing the beta chain
biosynthesis, synthesis, Lipooligosaccharide, genetics, LOS, Neisseria, strain, chain, locus, epitope, conservation, Gonorrhoeae, lgt, Neisseria gonorrhoeae, requirement
NCBI PubMed ID: 8879194Journal NLM ID: 2985109RPublisher: Rockefeller University Press
Institutions: Laboratory of Bacterial Pathogenesis and Immunology, Rockefeller University, New York, NY, USA
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12. Compound ID: 381
|
a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-+
|
a-D-GlcpNAc-(1-2)-+ | a-Kdop-(2-4)-+
| | |
EtN-(1--P--3)--L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130651,IEDB_130659,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152217,IEDB_175430,IEDB_190606,IEDB_2189047,IEDB_226300,IEDB_418765,IEDB_418766,IEDB_418767,IEDB_418768,IEDB_418769,IEDB_418770,IEDB_419428,IEDB_419429,IEDB_423106,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 120
Tsai C, Chen WH, Balakonis PA "Characterization of terminal NeuNAca2-3Galb1-4GlcNAc sequence in lipooligosaccharide of Neisseria meningitidis" -
Glycobiology 8(4) (1998) 359-365
Group B and C Neisseria meningitidis are the major cause of meningococcal disease in the United States and in Europe. N . meningitidis lipooligosaccharide (LOS), a major surface antigen, can be divided into 12 immunotypes of which L1 through L8 were found among Group B and C organisms. Groups B and C but not Group A may sialylate their LOSs with N-acetylneuraminic acid (NeuNAc) at the nonreducing end because they synthesize CMP-NeuNAc. Using sialic acid-galactose binding lectins as probes in an ELISA format, six of the eight LOS immunotypes (L2, L3, L4, L5, L7, and L8) in Groups B and C bound specifically to Maackia amurensis leukoagglutinin (MAL), which recognizes NeuNAcα2-3Galβ1-4GlcNAc/Glc sequence, but not to Sambucus nigra agglutinin, which binds NeuNAcα2-6Gal sequence. The combination of SDS-PAGE and MAL-blot analyses revealed that these six LOSs contained only the NeuNAcα2-3Galβ1-4GlcNAc trisaccharide sequence in their 4.1 kDa LOS components, which have a common terminal lacto-N-neotetraose (LNnT, Galβ1-4GlcNAcβ1-3Galβ1-4Glc) structure when nonsialylated as shown by previous studies. The LOS-lectin binding was abolished when the LOSs were treated with Newcastle disease viral neuraminidase which cleaves α2→3 linked sialic acid. Methylation analysis of a representative LOS (L2) confirmed that NeuNAc is 2→3 linked to Gal. Thus, these LOSs structurally mimic certain glycolipids, i.e., paragloboside (LNnT-ceramide) and sialylparagloboside and some glycoproteins in having LNnT and N-acetyllactosamine sequences, respectively, with or without α2→3 linked NeuNAc. The molecular mimicry of the LOSs may play a role in the pathogenesis of N.meningitidis by assisting the organism to evade host immune defenses in man.
LPS, structure, core, Lipooligosaccharide, Neisseria meningitidis, Neisseria, terminal, characterization, neuraminic acid, lactosamine, sequence
NCBI PubMed ID: 9499383Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Division of Bacterial Products, Center for Biologics Evaluation and Research, FDA, Bethesda, MD, USA.
Methods: methylation, ELISA
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13. Compound ID: 511
|
a-D-GlcpNAc-(1-2)-+
|
/Variants 0/-L-gro-a-D-manHepp-(1-3)-+ a-Kdop-(2-4)-+
| |
?%a-Neup5Ac-(2-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
/Variants 0/ is:
EtN-(1--P--3)--
OR (exclusively)
a-D-Glcp-(1-3)- |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130651,IEDB_130659,IEDB_136044,IEDB_136794,IEDB_136906,IEDB_137472,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150933,IEDB_151528,IEDB_151531,IEDB_152217,IEDB_175430,IEDB_190606,IEDB_2189047,IEDB_226300,IEDB_418765,IEDB_418766,IEDB_418767,IEDB_418768,IEDB_418769,IEDB_418770,IEDB_419428,IEDB_419429,IEDB_419430,IEDB_423106,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_167,SB_170,SB_171,SB_172,SB_178,SB_187,SB_192,SB_195,SB_31,SB_39,SB_6,SB_62,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 121
Tsai CM, Kao G, Zhu P "Influence of the length of the lipooligosaccharide a chain on its sialylation in Neisseria meningitidis" -
Infection and Immunity 70(1) (2002) 407-411
The sialylation of lipooligosaccharide (LOS) in Neisseria meningitidis plays a role in the resistance of the organism to killing by normal human serum. The length of the alpha chain extending out from the heptose I [Hep (I)] moiety of LOS influenced sialylation of N. meningitidis LOS in vitro and in vivo. The alpha chain required a terminal Gal and a trisaccharide or longer oligosaccharide to serve as an acceptor for sialylation. The disaccharide lactose (Galβ1-4Glc) in the alpha chain of immunotype L8 LOS could not function as an acceptor for the sialyltransferase, probably due to steric hindrance imposed by the neighboring Hep (II) with phosphorylethanolamine and another group attached.
Lipooligosaccharide, Neisseria meningitidis, sialyltransferase, structure-activity relationship, Substrate Specificity
NCBI PubMed ID: 11748209Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: tsai@cber.fda.gov
Institutions: Division of Bacterial, Parasitic, and Allergenic Products, Center for Biologics, Food and Drug Administration, Bethesda, MD, USA
Methods: SDS-PAGE
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14. Compound ID: 797
|
P-3)-+
|
a-D-GlcpN-(1-2)-L-gro-a-D-manHepp-(1-3)-+ a-Kdop-(2-4)-+ P-4)-+
| | |
a-Neup-(2-6)-a-D-Galp-(1-4)-b-D-Galp-(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: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130651,IEDB_130659,IEDB_135394,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_146664,IEDB_150908,IEDB_151528,IEDB_151531,IEDB_152217,IEDB_190606,IEDB_2189047,IEDB_423106,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 207
Wakarchuk WW, Gilbert M, Martin A, Wu YY, Brisson JR, Thibault P, Richards JC "Structure of an a-2,6-sialylated lipooligosaccharide from Neisseria meningitidis immunotype L1" -
European Journal of Biochemistry 254(3) (1998) 626-633
The recent cloning of the lipooligosaccharide (LOS) α-2,3-sialyltransferase from Neisseria meningitidis immunotype L3 permitted us to examine other immunotypes for this structural gene. We identified the gene and measured the enzyme activity in the L1 immunotype strain which had previously been reported to lack sialic acid in its LOS because it contains a terminal α-linked galactose which was thought not to be an acceptor for the sialyltransferase. This finding prompted us to re-examine the structure of the LOS from the L1 immunotype, which revealed the presence of sialic acid on the terminal α-linked galactose. Oligosaccharides derived from the LOS were shown to be sialylated by composition and methylation analysis, mass spectrometry and nuclear magnetic resonance. The detailed structural analysis showed the sialic acid to occur only at O6 of the teminal α-D-galactopyranose residue of the α-D-Gal-1,4-β-D-Gal-1,4-β-D-glc trisaccharide (Pk epitope) chain of the LOS, in the alfa-D configuration. These data are the first report of a α-2,6-linked sialic acid in a bacterial LOS or lipopolysaccharide, and also the first report of a sialylated Pk epitope.
structure, Lipooligosaccharide, Neisseria meningitidis, immunotype, Neisseria, sialyltransferase, glycosyltransferase
NCBI PubMed ID: 9688275Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: warren.wakarchuk@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ontario, Canada
Methods: NMR-2D, NMR, ESI-MS
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15. Compound ID: 873
|
a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-+
|
Cho-(1--P--6)--b-D-Galp-(1-2)-L-gro-a-D-manHepp-(1-2)-+ | EtN-(1---P---P---4)-+
| | |
a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-a-D-Glcp-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
|
EtN-(1--P--6)--+ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_120354,IEDB_123890,IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137338,IEDB_137472,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140624,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_148488,IEDB_151528,IEDB_152217,IEDB_190606,IEDB_2189047,IEDB_423106,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 244
Griffin R, Cox AD, Makepeace K, Richards JC, Moxon ER, Hood DW "The role of lex2 in lipopolysaccharide biosynthesis in Haemophilus influenzae strains RM7004 and RM153" -
Microbiology (2003) 3165-3175
The locus lex2, comprising lex2A and lex2B, contributes to the phase-variable expression of lipopolysaccharide (LPS) of Haemophilus influenzae and was found to be present in 74 % of strains investigated. lex2A contains 5'-GCAA repeats which vary in number from 4 to 46 copies between strains. The locus was cloned from the serotype b strains RM7004 and RM153 and showed >99 % nucleotide sequence identity between these strains and the published lex2 sequence. Disruption of the lex2B gene in strain RM7004 resulted in truncation of some LPS glycoforms, shown by gel fractionation, with only one glycoform reacting with a digalactoside-specific monoclonal antibody, 4C4, compared with four LPS glycoforms in the more elongated LPS of the parent strain. Mass spectrometry and NMR analyses of LPS from the lex2B mutant revealed loss of the terminal digalactoside as well as the second β-glucose extending from the first heptose of the inner core. The authors conclude that Lex2B is the β-(1-4)-glucosyltransferase that adds the second β-glucose to the first β-glucose as part of the oligosaccharide extension from the first heptose of the LPS of strain RM7004. Investigation of the expression of the lex2 locus indicated that the genes are co-transcribed and that both reading frames are required for addition of this second β-glucose in a phase-variable manner
Lipopolysaccharide, biosynthesis, Haemophilus influenzae, core, lipopolysaccharide biosynthesis, monoclonal antibodies, inner core
NCBI PubMed ID: 14600228Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: dhood@molbiol.ox.ac.uk
Institutions: Molecular Infectious Diseases Group, University of Oxford Department of Paediatrics, Weatherall Institute of Molecular Medicine, John Radcliffe Hospital, Headington, Oxford OX3 9DS, UK. Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A 0R6
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Next 15 structure(s)
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