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1. Compound ID: 873
a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-+
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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/
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EtN-(1--P--6)--+ |
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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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2. Compound ID: 2750
EtN-(1--P--6)--+
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EtN-(1--P--3)--L-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-+
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Cho-(1--P--6)--+ | EtN-(1---P---P---4)-+
| | |
b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137338,IEDB_137472,IEDB_137473,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_146664,IEDB_151528,IEDB_152217,IEDB_190606,IEDB_2189047,IEDB_241118,IEDB_423106,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_21,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 964
Mansson M, Hood DW, Moxon ER, Schweda EK "Structural characterization of a novel branching pattern in the lipopolysaccharide from nontypeable Haemophilus influenzae" -
European Journal of Biochemistry 270(14) (2003) 2979-2991
Lipopolysaccharide, Haemophilus, Haemophilus influenzae, structural, characterization, pattern
Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: elke.schweda@kfc.ki.se
Institutions: University College of south Stockholm, Clinical Research Centre, Huddinge, Sweden
Methods: NMR
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3. Compound ID: 2751
b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-+
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a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-+
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EtN-(1--P--6)--+ | EtN-(1---P---P---4)-+
| | |
EtN-(1--P--3)--L-gro-a-D-manHepp-(1-2)-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
Compound class: LPS
Contained glycoepitopes: 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_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_146664,IEDB_151528,IEDB_152217,IEDB_190606,IEDB_2189046,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: 964
Mansson M, Hood DW, Moxon ER, Schweda EK "Structural characterization of a novel branching pattern in the lipopolysaccharide from nontypeable Haemophilus influenzae" -
European Journal of Biochemistry 270(14) (2003) 2979-2991
Lipopolysaccharide, Haemophilus, Haemophilus influenzae, structural, characterization, pattern
Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: elke.schweda@kfc.ki.se
Institutions: University College of south Stockholm, Clinical Research Centre, Huddinge, Sweden
Methods: NMR
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4. Compound ID: 2771
a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-+
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b-D-Galp-(1-2)-L-gro-a-D-manHepp-(1-2)-+ |
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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-(2-6)-b-D-GlcpN-(1-6)-D-GlcN-ol |
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Structure type: oligomer
Contained glycoepitopes: IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137338,IEDB_137340,IEDB_137472,IEDB_137779,IEDB_138949,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_148488,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: 974
Masoud H, Martin A, Thibault P, Moxon ER, Richards JC "Structure of extended lipopolysaccharide glycoforms containing two globotriose units in Haemophilus influenzae serotype b(RM7004)" -
Biochemistry 42(15) (2003) 4463-4475
Lipopolysaccharide (LPS) is a major virulence determinant of the human bacterial pathogen Haemophilus influenzae. Structural elucidation of the LPS from H. influenzae type b(RM7004) was achieved by using electrospray ionization mass spectrometry (ESI-MS) and high-field NMR techniques on delipidated LPS and core oligosaccharide samples of LPS. It was found that the organism elaborates a series of related LPS glycoforms having a common inner-core structure, but differing in the number and position of attached hexose residues. LPS glycoforms containing between four and nine hexose residues were structurally characterized. The inner-core element was determined to be L-α-D-Hepp-(1→2)-[PEA→6]-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp-(1→5)-[P→4]-α-KDOp-(2→, a structural feature which has been identified in every H. influenzae strain investigated to date. Two major groups of isomeric glycoforms were characterized in which the terminal Hepp residue of the inner-core element was either substituted at the O-2 position with a β-D-Galp residue or not. The structures of the major LPS glycoforms were found to have oligosaccharide chain extensions from O-3 of the middle Hepp residue. Glycoforms containing five and six hexose residues were most abundant and were shown to carry the tetrasaccharide unit α-D-Galp-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→4)-α-D-Glcp at the O-3 position of the middle heptose. This tetrasaccharide displays the globoside trisaccharide (globotriose) as a terminal epitope, a structure that is found on many human cells (P(k) blood group antigen) and which is thought to be an important virulence determinant for H. influenzae. LPS glycoforms were characterized that had further chain extension from the β-D-Glcp-(1→ residue of the proximal Hepp. In the fully extended LPS (Hex9/Hex8' glycoforms), both the proximal and middle heptose residues carried tetrasaccharide chains displaying terminal globotriose epitopes. In addition, the LPS was found to carry phosphorylcholine and O-acetyl groups.
Lipopolysaccharide, NMR, Haemophilus influenzae, Haemophilus influenzae type b
NCBI PubMed ID: 12693942Publication DOI: 10.1021/bi026632aJournal NLM ID: 0370623Publisher: American Chemical Society
Correspondence: Jim.Richards@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Canada, Department of Biological Sciences, Faculty of Science, University of Jordan, Amman, Jordan, and Molecular Infectious Diseases Group, Department of Paediatrics, Institute for Molecular Medicine, John Radcliffe Hospital, Headington, Oxford 0X3 3DU, United Kingdom
Methods: NMR
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5. Compound ID: 2772
a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-+
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L-gro-a-D-manHepp-(1-2)-+ |
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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-(2-6)-b-D-GlcpN-(1-6)-D-GlcN-ol |
Show graphically |
Structure type: oligomer
Contained glycoepitopes: IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137338,IEDB_137340,IEDB_137472,IEDB_137779,IEDB_138949,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,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: 974
Masoud H, Martin A, Thibault P, Moxon ER, Richards JC "Structure of extended lipopolysaccharide glycoforms containing two globotriose units in Haemophilus influenzae serotype b(RM7004)" -
Biochemistry 42(15) (2003) 4463-4475
Lipopolysaccharide (LPS) is a major virulence determinant of the human bacterial pathogen Haemophilus influenzae. Structural elucidation of the LPS from H. influenzae type b(RM7004) was achieved by using electrospray ionization mass spectrometry (ESI-MS) and high-field NMR techniques on delipidated LPS and core oligosaccharide samples of LPS. It was found that the organism elaborates a series of related LPS glycoforms having a common inner-core structure, but differing in the number and position of attached hexose residues. LPS glycoforms containing between four and nine hexose residues were structurally characterized. The inner-core element was determined to be L-α-D-Hepp-(1→2)-[PEA→6]-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp-(1→5)-[P→4]-α-KDOp-(2→, a structural feature which has been identified in every H. influenzae strain investigated to date. Two major groups of isomeric glycoforms were characterized in which the terminal Hepp residue of the inner-core element was either substituted at the O-2 position with a β-D-Galp residue or not. The structures of the major LPS glycoforms were found to have oligosaccharide chain extensions from O-3 of the middle Hepp residue. Glycoforms containing five and six hexose residues were most abundant and were shown to carry the tetrasaccharide unit α-D-Galp-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→4)-α-D-Glcp at the O-3 position of the middle heptose. This tetrasaccharide displays the globoside trisaccharide (globotriose) as a terminal epitope, a structure that is found on many human cells (P(k) blood group antigen) and which is thought to be an important virulence determinant for H. influenzae. LPS glycoforms were characterized that had further chain extension from the β-D-Glcp-(1→ residue of the proximal Hepp. In the fully extended LPS (Hex9/Hex8' glycoforms), both the proximal and middle heptose residues carried tetrasaccharide chains displaying terminal globotriose epitopes. In addition, the LPS was found to carry phosphorylcholine and O-acetyl groups.
Lipopolysaccharide, NMR, Haemophilus influenzae, Haemophilus influenzae type b
NCBI PubMed ID: 12693942Publication DOI: 10.1021/bi026632aJournal NLM ID: 0370623Publisher: American Chemical Society
Correspondence: Jim.Richards@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Canada, Department of Biological Sciences, Faculty of Science, University of Jordan, Amman, Jordan, and Molecular Infectious Diseases Group, Department of Paediatrics, Institute for Molecular Medicine, John Radcliffe Hospital, Headington, Oxford 0X3 3DU, United Kingdom
Methods: NMR
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6. Compound ID: 2780
EtN-(1-0)-?%P---P--4)-+
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a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-+ |
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b-D-Galp-(1-2)-L-gro-a-D-manHepp-(1-2)-+ | |
| | |
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/
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EtN-(1--P--6)--+ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Contained glycoepitopes: 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_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: 974
Masoud H, Martin A, Thibault P, Moxon ER, Richards JC "Structure of extended lipopolysaccharide glycoforms containing two globotriose units in Haemophilus influenzae serotype b(RM7004)" -
Biochemistry 42(15) (2003) 4463-4475
Lipopolysaccharide (LPS) is a major virulence determinant of the human bacterial pathogen Haemophilus influenzae. Structural elucidation of the LPS from H. influenzae type b(RM7004) was achieved by using electrospray ionization mass spectrometry (ESI-MS) and high-field NMR techniques on delipidated LPS and core oligosaccharide samples of LPS. It was found that the organism elaborates a series of related LPS glycoforms having a common inner-core structure, but differing in the number and position of attached hexose residues. LPS glycoforms containing between four and nine hexose residues were structurally characterized. The inner-core element was determined to be L-α-D-Hepp-(1→2)-[PEA→6]-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp-(1→5)-[P→4]-α-KDOp-(2→, a structural feature which has been identified in every H. influenzae strain investigated to date. Two major groups of isomeric glycoforms were characterized in which the terminal Hepp residue of the inner-core element was either substituted at the O-2 position with a β-D-Galp residue or not. The structures of the major LPS glycoforms were found to have oligosaccharide chain extensions from O-3 of the middle Hepp residue. Glycoforms containing five and six hexose residues were most abundant and were shown to carry the tetrasaccharide unit α-D-Galp-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→4)-α-D-Glcp at the O-3 position of the middle heptose. This tetrasaccharide displays the globoside trisaccharide (globotriose) as a terminal epitope, a structure that is found on many human cells (P(k) blood group antigen) and which is thought to be an important virulence determinant for H. influenzae. LPS glycoforms were characterized that had further chain extension from the β-D-Glcp-(1→ residue of the proximal Hepp. In the fully extended LPS (Hex9/Hex8' glycoforms), both the proximal and middle heptose residues carried tetrasaccharide chains displaying terminal globotriose epitopes. In addition, the LPS was found to carry phosphorylcholine and O-acetyl groups.
Lipopolysaccharide, NMR, Haemophilus influenzae, Haemophilus influenzae type b
NCBI PubMed ID: 12693942Publication DOI: 10.1021/bi026632aJournal NLM ID: 0370623Publisher: American Chemical Society
Correspondence: Jim.Richards@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Canada, Department of Biological Sciences, Faculty of Science, University of Jordan, Amman, Jordan, and Molecular Infectious Diseases Group, Department of Paediatrics, Institute for Molecular Medicine, John Radcliffe Hospital, Headington, Oxford 0X3 3DU, United Kingdom
Methods: NMR
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7. Compound ID: 2781
EtN-(1-0)-?%P---P--4)-+
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a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-+ |
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EtN-(1--P--6)--+ | |
| | |
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/
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L-gro-a-D-manHepp-(1-2)-+ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Contained glycoepitopes: 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_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,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: 974
Masoud H, Martin A, Thibault P, Moxon ER, Richards JC "Structure of extended lipopolysaccharide glycoforms containing two globotriose units in Haemophilus influenzae serotype b(RM7004)" -
Biochemistry 42(15) (2003) 4463-4475
Lipopolysaccharide (LPS) is a major virulence determinant of the human bacterial pathogen Haemophilus influenzae. Structural elucidation of the LPS from H. influenzae type b(RM7004) was achieved by using electrospray ionization mass spectrometry (ESI-MS) and high-field NMR techniques on delipidated LPS and core oligosaccharide samples of LPS. It was found that the organism elaborates a series of related LPS glycoforms having a common inner-core structure, but differing in the number and position of attached hexose residues. LPS glycoforms containing between four and nine hexose residues were structurally characterized. The inner-core element was determined to be L-α-D-Hepp-(1→2)-[PEA→6]-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp-(1→5)-[P→4]-α-KDOp-(2→, a structural feature which has been identified in every H. influenzae strain investigated to date. Two major groups of isomeric glycoforms were characterized in which the terminal Hepp residue of the inner-core element was either substituted at the O-2 position with a β-D-Galp residue or not. The structures of the major LPS glycoforms were found to have oligosaccharide chain extensions from O-3 of the middle Hepp residue. Glycoforms containing five and six hexose residues were most abundant and were shown to carry the tetrasaccharide unit α-D-Galp-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→4)-α-D-Glcp at the O-3 position of the middle heptose. This tetrasaccharide displays the globoside trisaccharide (globotriose) as a terminal epitope, a structure that is found on many human cells (P(k) blood group antigen) and which is thought to be an important virulence determinant for H. influenzae. LPS glycoforms were characterized that had further chain extension from the β-D-Glcp-(1→ residue of the proximal Hepp. In the fully extended LPS (Hex9/Hex8' glycoforms), both the proximal and middle heptose residues carried tetrasaccharide chains displaying terminal globotriose epitopes. In addition, the LPS was found to carry phosphorylcholine and O-acetyl groups.
Lipopolysaccharide, NMR, Haemophilus influenzae, Haemophilus influenzae type b
NCBI PubMed ID: 12693942Publication DOI: 10.1021/bi026632aJournal NLM ID: 0370623Publisher: American Chemical Society
Correspondence: Jim.Richards@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Canada, Department of Biological Sciences, Faculty of Science, University of Jordan, Amman, Jordan, and Molecular Infectious Diseases Group, Department of Paediatrics, Institute for Molecular Medicine, John Radcliffe Hospital, Headington, Oxford 0X3 3DU, United Kingdom
Methods: NMR
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8. Compound ID: 4081
a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-+
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Cho-(1--P--6)--b-D-Galp-(1-2)-L-gro-a-D-manHepp-(1-2)-+ | EtN-(1--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: 1514
Griffin R, Cox AD, Makepeace K, Richards JC, Moxon ER, Hood DW "Elucidation of the Monoclonal Antibody 5G8-Reactive, Virulence-Associated Lipopolysaccharide Epitope of Haemophilus influenzae and Its Role in Bacterial Resistance to Complement-Mediated Killing" -
Infection and Immunity 73(4) (2005) 2213-2221
The phase-variable locus lex2 is required for expression of a Haemophilus influenzae lipopolysaccharide (LPS) epitope of previously unknown structure. This epitope, which is reactive with monoclonal antibody (MAb) 5G8, has been associated with virulence of type b strains. When strain RM118 (from the same source as strain Rd), in which the lex2 locus and MAb 5G8 reactivity are absent, was transformed with lex2 DNA, transformants that were reactive with MAb 5G8 were obtained. Surprisingly, the 5G8 reactivity of these transformants was phase variable, although the lex2 locus lacked tetrameric repeats and was constitutively expressed. This phase variation was shown to be the result of phase-variable expression of phosphorylcholine (PCho) such that MAb 5G8 reacted only in the absence of PCho. Structural analysis showed that, compared to RM118, the lex2 transformant had acquired a tetrasaccharide, Gal-α1,4-Gal-β1,4-Glc-β1,4-Glc-β1,4, linked to the proximal heptose (HepI). A terminal GalNAc was detected in a minority of glycoforms. LPS derived from a mutant of RM7004, a virulent type b strain which naturally expresses lex2 and has LPS containing the same tetrasaccharide linked to HepI as the sole oligosaccharide extension from the inner core, confirmed that GalNAc is not a part of the MAb 5G8-reactive epitope. Thus, MAb 5G8 specifically binds to the structure Gal-α1,4-Gal-β1,4-Glc-β1,4-Glc-β attached via a 1,4 linkage to HepI of H. influenzae LPS, and we show that the ability to synthesize this novel tetrasaccharide was associated with enhanced bacterial resistance to complement-mediated killing
Lipopolysaccharide, Haemophilus, Haemophilus influenzae, LPS, oligosaccharide, structure, core, heptose, tetrasaccharide, Phase variation, expression, Bacterial, microbiology, phase, role, DNA, strain, structural, terminal, variation, virulence, analysis, structural analysis, linked, molecular, locus, antibodies, antibody, epitope, monoclonal, monoclonal antibodies, monoclonal antibody, type, enhanced, infection, level, MAb, mutant, linkage, inner core, elucidation, resistance, ability, killing, phosphorylcholine, virulent, variable, reactivity, source, absence
NCBI PubMed ID: 15784565Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: r.griffin@imperial.ac.uk
Institutions: Centre for Molecular Microbiology and Infection, Level 3, Flowers Building, Imperial College, London SW7 2AZ, United Kingdom
Methods: serological methods, genetic methods
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9. Compound ID: 4309
a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-+
|
b-D-Galp-(1-2)-L-gro-a-D-manHepp-(1-2)-+ | 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/ |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: 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_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: 1614
Griffin R, Bayliss CD, Herbert MA, Cox AD, Makepeace K, Richards JC, Hood DW, Moxon ER "Digalactoside expression in the lipopolysaccharide of Haemophilus influenzae and its role in intravascular survival" -
Infection and Immunity 73(10) (2005) 7022-7026
Digalactoside (galα-1-4 galβ) structures of the lipopolysaccharide (LPS) of Haemophilus influenzae are implicated in virulence. A confounding factor is that tetranucleotide repeats within the lic2A, lgtC, and lex2 genes mediate phase-variable expression of the digalactosides. By deleting these repeats, we constructed recombinant strains of RM153 constitutively expressing either one or two LPS digalactosides. Expression of two digalactosides, rather than one, was associated with increased virulence of H. influenzae in vivo.
Lipopolysaccharide, Haemophilus, Haemophilus influenzae, LPS, structure, disease, expression, gene, role, strain, virulence, group, molecular, factor, infectious disease, medicine, Infectious, recombinant, in vivo, survival
NCBI PubMed ID: 16177385Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: r.griffin@imperial.ac.uk
Institutions: Molecular Infectious Diseases Group, University of Oxford Department of Paediatrics, Weatherall Institute of Molecular Medicine, John Radcliffe Hospital, Headington, UK
Methods: genetic methods
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10. Compound ID: 7380
b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1--/(1->4) core Hep I/ |
Show graphically |
Structure type: fragment of a bigger structure
Aglycon: (1->4) core Hep I
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137338,IEDB_137472,IEDB_137473,IEDB_1391964,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,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_21,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 3345
Schweda EK, Richards JC, Hood DW, Moxon ER "Expression and structural diversity of the lipopolysaccharide of Haemophilus influenzae: implication in virulence" -
International Journal of Medical Microbiology 297(5) (2007) 297-306
Lipopolysaccharide (LPS) is a major virulence determinant of the human bacterial pathogen Haemophilus influenzae. A characteristic feature of H. influenzae LPS is the extensive intra- and inter-strain heterogeneity of glycoform structure which is key to the role of the molecule in both commensal and disease-causing behaviour of the bacterium. Through the combination of genetics and detailed structural analyses, H. influenzae is an exemplar Gram-negative bacterium for which now the most extensive and detailed LPS structural data and functional correlates are available. LPS from H. influenzae consists of a conserved glucose-substituted triheptosyl inner-core moiety L-α-D-Hepp-(1→2)-[PEtn→6]-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp linked to lipid A via Kdo 4-phosphate. The inner-core unit provides the template for attachment of oligosaccharide- and non-carbohydrate substituents. Here, the structure, genetics and expression of LPS glycoforms in the outer core are reviewed as well as their implication on virulence
Lipopolysaccharide, Haemophilus influenzae, molecular mimicry, Phosphocholine, sialic acid, Digalactoside
NCBI PubMed ID: 17452015Publication DOI: 10.1016/j.ijmm.2007.03.007Journal NLM ID: 100898849Publisher: Jena, Germany: Urban & Fischer Verlag
Correspondence: elke.schweda@crc.ki.se
Institutions: Clinical Research Centre, Karolinska Institutet and University College of South Stockholm, NOVUM, S-141 86 Huddinge, Sweden
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11. Compound ID: 7381
b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-+
|
b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1--/(1->4) core Hep I/ |
Show graphically |
Structure type: fragment of a bigger structure
Aglycon: (1->4) core Hep I
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137338,IEDB_137472,IEDB_137473,IEDB_1391964,IEDB_139428,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_146664,IEDB_151528,IEDB_152217,IEDB_190606,IEDB_2189046,IEDB_423106,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_21,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 3345
Schweda EK, Richards JC, Hood DW, Moxon ER "Expression and structural diversity of the lipopolysaccharide of Haemophilus influenzae: implication in virulence" -
International Journal of Medical Microbiology 297(5) (2007) 297-306
Lipopolysaccharide (LPS) is a major virulence determinant of the human bacterial pathogen Haemophilus influenzae. A characteristic feature of H. influenzae LPS is the extensive intra- and inter-strain heterogeneity of glycoform structure which is key to the role of the molecule in both commensal and disease-causing behaviour of the bacterium. Through the combination of genetics and detailed structural analyses, H. influenzae is an exemplar Gram-negative bacterium for which now the most extensive and detailed LPS structural data and functional correlates are available. LPS from H. influenzae consists of a conserved glucose-substituted triheptosyl inner-core moiety L-α-D-Hepp-(1→2)-[PEtn→6]-L-α-D-Hepp-(1→3)-[β-D-Glcp-(1→4)]-L-α-D-Hepp linked to lipid A via Kdo 4-phosphate. The inner-core unit provides the template for attachment of oligosaccharide- and non-carbohydrate substituents. Here, the structure, genetics and expression of LPS glycoforms in the outer core are reviewed as well as their implication on virulence
Lipopolysaccharide, Haemophilus influenzae, molecular mimicry, Phosphocholine, sialic acid, Digalactoside
NCBI PubMed ID: 17452015Publication DOI: 10.1016/j.ijmm.2007.03.007Journal NLM ID: 100898849Publisher: Jena, Germany: Urban & Fischer Verlag
Correspondence: elke.schweda@crc.ki.se
Institutions: Clinical Research Centre, Karolinska Institutet and University College of South Stockholm, NOVUM, S-141 86 Huddinge, Sweden
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12. Compound ID: 9902
L-gro-a-D-manHepp?Ac-(1-2)-+
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EtN-(1--P--6)--L-gro-a-D-manHepp-(1-3)-+
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a-Neup5Ac-(2-8)-a-Neup5Ac-(2-3)-+ Cho-(1--P--6)--+ |
| | |
b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp?Ac-(1-4)-L-gro-a-D-manHepp-(1-5)-Sug
Sug = anhKdo-ol |
Show graphically |
Structure type: oligomer
Trivial name: disialylated glycoform
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130651,IEDB_130676,IEDB_130679,IEDB_136044,IEDB_136794,IEDB_136906,IEDB_137338,IEDB_137472,IEDB_137473,IEDB_137779,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140624,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150933,IEDB_150937,IEDB_151528,IEDB_152217,IEDB_153198,IEDB_153199,IEDB_190606,IEDB_2189047,IEDB_241118,IEDB_423106,IEDB_742247,IEDB_858580,IEDB_983931,SB_116,SB_165,SB_166,SB_167,SB_170,SB_171,SB_172,SB_178,SB_187,SB_192,SB_195,SB_21,SB_31,SB_35,SB_37,SB_39,SB_42,SB_6,SB_61,SB_62,SB_68,SB_7,SB_76,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 4125
Twelkmeyer B, Burstrom PK, Li J, Richard ME, Hood DW, Schweda EK "Expression of a new disialyllacto structure in the lipopolysaccharide of non-typeable Haemophilus influenzae" -
Carbohydrate Research 346(13) (2011) 1885-1897
The structure of lipopolysaccharide (LPS) expressed by non-typeable Haemophilus influenzae (NTHi) strains 1008 and 1247 has been investigated by mass spectrometry and NMR analyses on O-deacylated LPS and core oligosaccharide material. Both strains express the conserved triheptosyl inner core, [L-α-D-Hepp-(1→2)-[PEtn→6]-L-α-D-Hepp-(1→3)-L-α-D-Hepp-(1→5)-[PPEtn→4]-α-Kdo-(2→6)-Lipid A] with PCho→6)-β-D-Glcp (GlcI) substituting the proximal heptose (HepI) at O-4. Strain 1247 expresses the common structural motifs of H. influenzae; globotetraose [β-D-GalpNAc-(1→3)-α-D-Galp-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→] and its truncated versions globoside [α-D-Galp-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→] and lactose [β-D-Galp-(1→4)-β-D-Glcp-(1→] linked to the terminal heptose of the inner core and GlcI. A genetically distinct NTHi strain, 1008, expresses identical structures to strain 1247 with the exception that it lacks GalNAc. A lpsA mutant of strain 1247 expressed LPS of reduced complexity that facilitated unambiguous structural determination of the oligosaccharide from HepI. By CE-ESI-MS/MS we identified disialylated glycoforms indicating disialyllactose [α-Neu5Ac-(2→8)-α-Neu5Ac-(2→3)-β-D-Gal-(1→4)-β-D-Glcp-(1→] as an extension from GlcI which is a novel finding for NTHi LPS.
Lipopolysaccharide, Haemophilus influenzae, otitis media, Digalactoside, disialyllactoside
NCBI PubMed ID: 21683945Publication DOI: 10.1016/j.carres.2011.05.020Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: E.K.H. Schweda
Institutions: Karolinska Institutet, Clinical Research Centre, Huddinge, Sweden
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, HF solvolysis, ESI-MS, mild acid hydrolysis, de-O-acylation with hydrazine, composition analysis, NMR-1D, alkaline deacylation, HPAEC-PAD, CE-ESI-MS/MS, CE-ESI-MS, LC-ESI-MS
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13. Compound ID: 9903
L-gro-a-D-manHepp?Ac-(1-2)-+
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EtN-(1--P--6)--L-gro-a-D-manHepp-(1-3)-+
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Cho-(1--P--6)--+ |
| |
b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp?Ac-(1-4)-L-gro-a-D-manHepp-(1-5)-Sug
Sug = anhKdo-ol |
Show graphically |
Structure type: oligomer
Trivial name: HexNAcHex4 glycoform
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137338,IEDB_137472,IEDB_137473,IEDB_137779,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140624,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_146664,IEDB_151528,IEDB_152217,IEDB_190606,IEDB_2189047,IEDB_241118,IEDB_423106,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_21,SB_31,SB_6,SB_61,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 4125
Twelkmeyer B, Burstrom PK, Li J, Richard ME, Hood DW, Schweda EK "Expression of a new disialyllacto structure in the lipopolysaccharide of non-typeable Haemophilus influenzae" -
Carbohydrate Research 346(13) (2011) 1885-1897
The structure of lipopolysaccharide (LPS) expressed by non-typeable Haemophilus influenzae (NTHi) strains 1008 and 1247 has been investigated by mass spectrometry and NMR analyses on O-deacylated LPS and core oligosaccharide material. Both strains express the conserved triheptosyl inner core, [L-α-D-Hepp-(1→2)-[PEtn→6]-L-α-D-Hepp-(1→3)-L-α-D-Hepp-(1→5)-[PPEtn→4]-α-Kdo-(2→6)-Lipid A] with PCho→6)-β-D-Glcp (GlcI) substituting the proximal heptose (HepI) at O-4. Strain 1247 expresses the common structural motifs of H. influenzae; globotetraose [β-D-GalpNAc-(1→3)-α-D-Galp-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→] and its truncated versions globoside [α-D-Galp-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→] and lactose [β-D-Galp-(1→4)-β-D-Glcp-(1→] linked to the terminal heptose of the inner core and GlcI. A genetically distinct NTHi strain, 1008, expresses identical structures to strain 1247 with the exception that it lacks GalNAc. A lpsA mutant of strain 1247 expressed LPS of reduced complexity that facilitated unambiguous structural determination of the oligosaccharide from HepI. By CE-ESI-MS/MS we identified disialylated glycoforms indicating disialyllactose [α-Neu5Ac-(2→8)-α-Neu5Ac-(2→3)-β-D-Gal-(1→4)-β-D-Glcp-(1→] as an extension from GlcI which is a novel finding for NTHi LPS.
Lipopolysaccharide, Haemophilus influenzae, otitis media, Digalactoside, disialyllactoside
NCBI PubMed ID: 21683945Publication DOI: 10.1016/j.carres.2011.05.020Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: E.K.H. Schweda
Institutions: Karolinska Institutet, Clinical Research Centre, Huddinge, Sweden
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, HF solvolysis, ESI-MS, mild acid hydrolysis, de-O-acylation with hydrazine, composition analysis, NMR-1D, alkaline deacylation, HPAEC-PAD, CE-ESI-MS/MS, CE-ESI-MS, LC-ESI-MS
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14. Compound ID: 9904
EtN-(1-0)-?%P---P--4)-+
|
Cho-(1--P--6)--+ |
| |
b-D-GalpNAc-(1-3)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-+ |
| |
EtN-(1--P--6)--+ | |
| | |
a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-2)-L-gro-a-D-manHepp-(1-2)-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
Trivial name: HexNAcHex7 glycoform
Compound class: LPS
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137338,IEDB_137472,IEDB_137473,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_146664,IEDB_151528,IEDB_152217,IEDB_190606,IEDB_2189047,IEDB_241118,IEDB_423106,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_21,SB_31,SB_6,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 4125
Twelkmeyer B, Burstrom PK, Li J, Richard ME, Hood DW, Schweda EK "Expression of a new disialyllacto structure in the lipopolysaccharide of non-typeable Haemophilus influenzae" -
Carbohydrate Research 346(13) (2011) 1885-1897
The structure of lipopolysaccharide (LPS) expressed by non-typeable Haemophilus influenzae (NTHi) strains 1008 and 1247 has been investigated by mass spectrometry and NMR analyses on O-deacylated LPS and core oligosaccharide material. Both strains express the conserved triheptosyl inner core, [L-α-D-Hepp-(1→2)-[PEtn→6]-L-α-D-Hepp-(1→3)-L-α-D-Hepp-(1→5)-[PPEtn→4]-α-Kdo-(2→6)-Lipid A] with PCho→6)-β-D-Glcp (GlcI) substituting the proximal heptose (HepI) at O-4. Strain 1247 expresses the common structural motifs of H. influenzae; globotetraose [β-D-GalpNAc-(1→3)-α-D-Galp-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→] and its truncated versions globoside [α-D-Galp-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→] and lactose [β-D-Galp-(1→4)-β-D-Glcp-(1→] linked to the terminal heptose of the inner core and GlcI. A genetically distinct NTHi strain, 1008, expresses identical structures to strain 1247 with the exception that it lacks GalNAc. A lpsA mutant of strain 1247 expressed LPS of reduced complexity that facilitated unambiguous structural determination of the oligosaccharide from HepI. By CE-ESI-MS/MS we identified disialylated glycoforms indicating disialyllactose [α-Neu5Ac-(2→8)-α-Neu5Ac-(2→3)-β-D-Gal-(1→4)-β-D-Glcp-(1→] as an extension from GlcI which is a novel finding for NTHi LPS.
Lipopolysaccharide, Haemophilus influenzae, otitis media, Digalactoside, disialyllactoside
NCBI PubMed ID: 21683945Publication DOI: 10.1016/j.carres.2011.05.020Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: E.K.H. Schweda
Institutions: Karolinska Institutet, Clinical Research Centre, Huddinge, Sweden
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, HF solvolysis, ESI-MS, mild acid hydrolysis, de-O-acylation with hydrazine, composition analysis, NMR-1D, alkaline deacylation, HPAEC-PAD, CE-ESI-MS/MS, CE-ESI-MS, LC-ESI-MS
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15. Compound ID: 9905
EtN-(1-0)-?%P---P--4)-+
|
Cho-(1--P--6)--+ |
| |
a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-+ |
| |
EtN-(1--P--6)--+ | |
| | |
a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-2)-L-gro-a-D-manHepp-(1-2)-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
Trivial name: Hex7 glycoform
Compound class: LPS
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_146664,IEDB_151528,IEDB_152217,IEDB_190606,IEDB_2189047,IEDB_241118,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: 4125
Twelkmeyer B, Burstrom PK, Li J, Richard ME, Hood DW, Schweda EK "Expression of a new disialyllacto structure in the lipopolysaccharide of non-typeable Haemophilus influenzae" -
Carbohydrate Research 346(13) (2011) 1885-1897
The structure of lipopolysaccharide (LPS) expressed by non-typeable Haemophilus influenzae (NTHi) strains 1008 and 1247 has been investigated by mass spectrometry and NMR analyses on O-deacylated LPS and core oligosaccharide material. Both strains express the conserved triheptosyl inner core, [L-α-D-Hepp-(1→2)-[PEtn→6]-L-α-D-Hepp-(1→3)-L-α-D-Hepp-(1→5)-[PPEtn→4]-α-Kdo-(2→6)-Lipid A] with PCho→6)-β-D-Glcp (GlcI) substituting the proximal heptose (HepI) at O-4. Strain 1247 expresses the common structural motifs of H. influenzae; globotetraose [β-D-GalpNAc-(1→3)-α-D-Galp-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→] and its truncated versions globoside [α-D-Galp-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→] and lactose [β-D-Galp-(1→4)-β-D-Glcp-(1→] linked to the terminal heptose of the inner core and GlcI. A genetically distinct NTHi strain, 1008, expresses identical structures to strain 1247 with the exception that it lacks GalNAc. A lpsA mutant of strain 1247 expressed LPS of reduced complexity that facilitated unambiguous structural determination of the oligosaccharide from HepI. By CE-ESI-MS/MS we identified disialylated glycoforms indicating disialyllactose [α-Neu5Ac-(2→8)-α-Neu5Ac-(2→3)-β-D-Gal-(1→4)-β-D-Glcp-(1→] as an extension from GlcI which is a novel finding for NTHi LPS.
Lipopolysaccharide, Haemophilus influenzae, otitis media, Digalactoside, disialyllactoside
NCBI PubMed ID: 21683945Publication DOI: 10.1016/j.carres.2011.05.020Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: E.K.H. Schweda
Institutions: Karolinska Institutet, Clinical Research Centre, Huddinge, Sweden
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, HF solvolysis, ESI-MS, mild acid hydrolysis, de-O-acylation with hydrazine, composition analysis, NMR-1D, alkaline deacylation, HPAEC-PAD, CE-ESI-MS/MS, CE-ESI-MS, LC-ESI-MS
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