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1. Compound ID: 338
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a-D-Glcp-(1-6)-+
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a-D-Glcp-(1-4)-b-D-Galp-(1-6)-b-D-Glcp-(1-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-Neu5Ac |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146100,IEDB_146664,IEDB_147450,IEDB_149174,IEDB_190606,IEDB_423085,IEDB_983931,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_23,SB_24,SB_7,SB_8,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 95
Gamian A, Ulrich J, Defaye J, Mieszala M, Witkowska D, Romanowska E "Structural heterogeneity of the sialic-acid-containing oligosaccharides from the lipopolysaccharide of Hafnia alvei strain 2 as detected by FABMS studies" -
Carbohydrate Research 314(3-4) (1998) 201-209
The structure of four oligosaccharide fractions from the Hafnia alvei strain 2 lipopolysaccharide (LPS) have been assigned by FABMS. This approach corroborates data previously established by NMR spectroscopy for the major oligosaccharides in these fractions [A. Gamian, E. Romanowska, U. Dabrowski, J. Dabrowski, Biochemistry 30 (1991) 5032-5038; E. Katzenellenbogen, A. Gamian, E. Romanowska, U. Dabrowski, J. Dabrowski, Biochem. Biophys. Res. Commun. 194 (1993) 1058-1064; N. Ravenscroft, A. Gamian, E. Romanowska, Eur. J. Biochem. 227 (1995) 889-896]. In addition, the MS/MS with B/E linked scan technique allowed the detection of an additional oligosaccharide with the structure: [formula: see text] lacking the branched O-6 linked glucopyranose residue at the 3-linked Gal unit, which indicates a structural heterogeneity for the major oligosaccharide fraction
Lipopolysaccharide, core oligosaccharide, Hafnia alvei, FABMS, sialic acid
NCBI PubMed ID: 10335589Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: gamian@immuno.iitd.pan.wroc.pl
Institutions: Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Wroclaw, Poland
Methods: FAB-MS, FAB-MS/MS
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2. Compound ID: 339
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a-D-Glcp-(1-6)-+
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a-D-Glcp-(1-6)-+ |
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a-D-Glcp-(1-4)-b-D-Galp-(1-6)-b-D-Glcp-(1-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-Neu5Ac |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146100,IEDB_146664,IEDB_147450,IEDB_149174,IEDB_190606,IEDB_423085,IEDB_983931,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_23,SB_24,SB_7,SB_8,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 95
Gamian A, Ulrich J, Defaye J, Mieszala M, Witkowska D, Romanowska E "Structural heterogeneity of the sialic-acid-containing oligosaccharides from the lipopolysaccharide of Hafnia alvei strain 2 as detected by FABMS studies" -
Carbohydrate Research 314(3-4) (1998) 201-209
The structure of four oligosaccharide fractions from the Hafnia alvei strain 2 lipopolysaccharide (LPS) have been assigned by FABMS. This approach corroborates data previously established by NMR spectroscopy for the major oligosaccharides in these fractions [A. Gamian, E. Romanowska, U. Dabrowski, J. Dabrowski, Biochemistry 30 (1991) 5032-5038; E. Katzenellenbogen, A. Gamian, E. Romanowska, U. Dabrowski, J. Dabrowski, Biochem. Biophys. Res. Commun. 194 (1993) 1058-1064; N. Ravenscroft, A. Gamian, E. Romanowska, Eur. J. Biochem. 227 (1995) 889-896]. In addition, the MS/MS with B/E linked scan technique allowed the detection of an additional oligosaccharide with the structure: [formula: see text] lacking the branched O-6 linked glucopyranose residue at the 3-linked Gal unit, which indicates a structural heterogeneity for the major oligosaccharide fraction
Lipopolysaccharide, core oligosaccharide, Hafnia alvei, FABMS, sialic acid
NCBI PubMed ID: 10335589Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: gamian@immuno.iitd.pan.wroc.pl
Institutions: Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Wroclaw, Poland
Methods: FAB-MS, FAB-MS/MS
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3. Compound ID: 1261
Structure type: oligomer
Contained glycoepitopes: IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_149174,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_423085,IEDB_983931,SB_192,SB_7
The structure is contained in the following publication(s):
- Article ID: 396
Torgov VI, Shashkov AS, Jann B, Jann K "NMR reinvestigation of two N-acetylneuraminic acid-containing O-specific polysaccharides (O56 and O24) of Escherichia coli" -
Carbohydrate Research 272(1) (1995) 73-90
Structures for the N-acetylneuraminic acid (Neu5Ac)-containing O56 and O24 polysaccharides of Escherichia coli have been reported previously. During these studies unusual chemical shifts had been observed for the NMR signals for H-3eq and C-3 of the Neu5Ac residues of both polysaccharides. In further pursuing this phenomenon, we have reinvestigated the O56 and O24 polysaccharides as well as derived oligosaccharides by one- and two-dimensional NMR spectroscopy. The results showed that structures of both polysaccharides (PSs) had to be modified and formulated as [formula: see text] 2D ROESY spectra revealed a strong NOE between H-3eq of Neu5Ac and the protons of the side-chain sugar (H-3 and H-5 of α-D-Galp in the O56 PS and H-3 of α-D-Glcp in the O24 PS) and also between H-3ax of Neu5Ac and H-3 of β-D-Glcp in the main chain. This indicated a close spatial association of the seven-linked α-Neu5Ac and the side-chain residues α-D-Galp (O56 PS) and α-D-Glcp (O25 PS), respectively. The strong long-range spatial contacts caused the unusual chemical shifts of H-3eq and C-3 of Neu5Ac.
Escherichia coli, NMR spectroscopy, polysaccharide structure, 024 and 056 antigens
NCBI PubMed ID: 7544238Publication DOI: 10.1016/0008-6215(95)00041-QJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: torgov@ioc.ac.ru
Institutions: Max-Planck-Institut für Immunbiologie, Freiburg, Germany
Methods: NMR-2D, NMR, sugar analysis, Smith degradation
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4. Compound ID: 1262
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a-D-Galp-(1-2)-+
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a-D-Galp-(1-2)-b-D-Glcp-(1-3)-b-D-GlcpNAc-(1-7)-a-Neup5Ac-(2-3)-b-D-Glcp-(1-3)-b-D-GlcpNAc-(1-7)-b-Neup5Ac |
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Structure type: oligomer
Contained glycoepitopes: IEDB_135813,IEDB_136794,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_423085,IEDB_983931,SB_170,SB_171,SB_172,SB_192,SB_7,SB_84
The structure is contained in the following publication(s):
- Article ID: 396
Torgov VI, Shashkov AS, Jann B, Jann K "NMR reinvestigation of two N-acetylneuraminic acid-containing O-specific polysaccharides (O56 and O24) of Escherichia coli" -
Carbohydrate Research 272(1) (1995) 73-90
Structures for the N-acetylneuraminic acid (Neu5Ac)-containing O56 and O24 polysaccharides of Escherichia coli have been reported previously. During these studies unusual chemical shifts had been observed for the NMR signals for H-3eq and C-3 of the Neu5Ac residues of both polysaccharides. In further pursuing this phenomenon, we have reinvestigated the O56 and O24 polysaccharides as well as derived oligosaccharides by one- and two-dimensional NMR spectroscopy. The results showed that structures of both polysaccharides (PSs) had to be modified and formulated as [formula: see text] 2D ROESY spectra revealed a strong NOE between H-3eq of Neu5Ac and the protons of the side-chain sugar (H-3 and H-5 of α-D-Galp in the O56 PS and H-3 of α-D-Glcp in the O24 PS) and also between H-3ax of Neu5Ac and H-3 of β-D-Glcp in the main chain. This indicated a close spatial association of the seven-linked α-Neu5Ac and the side-chain residues α-D-Galp (O56 PS) and α-D-Glcp (O25 PS), respectively. The strong long-range spatial contacts caused the unusual chemical shifts of H-3eq and C-3 of Neu5Ac.
Escherichia coli, NMR spectroscopy, polysaccharide structure, 024 and 056 antigens
NCBI PubMed ID: 7544238Publication DOI: 10.1016/0008-6215(95)00041-QJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: torgov@ioc.ac.ru
Institutions: Max-Planck-Institut für Immunbiologie, Freiburg, Germany
Methods: NMR-2D, NMR, sugar analysis, Smith degradation
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5. Compound ID: 3302
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GroN-(2-6)-+
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GroN-(2-6)-b-D-GalpA-(1-3)-b-D-GlcpNAc-(1-3)-a-D-GalpA-(1-4)-Neu5Ac |
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Structure type: oligomer
Contained glycoepitopes: IEDB_135813,IEDB_136794,IEDB_137340,IEDB_141807,IEDB_146100,IEDB_149174,IEDB_151531,IEDB_423085,SB_170,SB_171,SB_172,SB_84
The structure is contained in the following publication(s):
- Article ID: 1218
Shashkov AS, Senchenkova SN, Nazarenko EL, Zubkov VA, Gorshkova NM, Knirel YA, Gorshkova RP "Structure of the acidic polysaccharide chain of the lipopolysaccharide of Shewanella algae 48055" -
Carbohydrate Research 309(1) (1998) 103-108
A lipopolysaccharide (LPS) with an acidic polysaccharide chain was isolated from the bacterium Shewanella alga strain 48055 and cleaved selectively at the glycosidic linkage of N-acetylneuraminic acid to give a tetrasaccharide. Studies of the tetrasaccharide and the O-deacylated LPS by 1H and 13C NMR spectroscopy, including 2D COSY, TOCSY, NOESY, rotating-frame NOE spectroscopy (ROESY), and H-detected 1H, 13C heteronuclear multiple-quantum coherence (HMQC) experiments, revealed the following structure of the polysaccharide repeating unit: →3)-β-D-GalpA6GroN-(1→3)-β-D-GlcpNAc-(1→3)-α-D-GalpA6GroN-(1→4)-α-Neup5Ac-(2→ where GroN is an amidically linked residue of 2-amino-1,3-propanediol (2-amino-2-deoxyglycerol). A similar structure, but with 2-acetamido-2,6-dideoxy-D-glucose instead of 2-acetamido-2-deoxy-D-glucose, has been reported previously for the polysaccharide chain of a non-O1 Vibrio cholerae H11 LPS [E. V. Vinogradov, O. Holst, J.E. Thomas-Oates, K.W. Broady, and H. Brade, Eur. J. Biochem., 210 (1992) 491-498].
Lipopolysaccharide, LPS, structure, strain, polysaccharide, chain, acidic, acidic polysaccharide, NMR spectroscopy, O-specific, O-specific polysaccharide, sialic acid, Shewanella, N-acetylneuraminic acid, Neu5Ac, D-galacturonic acid, 2-amino-1, 3-propanediol, alga, Shewanella alga, 2-Amino-2-deoxyglycerol, Shewanella algae
NCBI PubMed ID: 9720241Publication DOI: 10.1016/S0008-6215(98)00127-XJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: knirel@ioc.ac.ru
Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: NMR
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6. Compound ID: 4314
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Neup5Ac-(2-6)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-D-manHepp-(1--/rest of core-lipid A/ |
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Structure type: oligomer
Aglycon: rest of core-lipid A
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_136044,IEDB_136794,IEDB_136906,IEDB_137472,IEDB_138950,IEDB_140087,IEDB_141495,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_149558,IEDB_151528,IEDB_158551,IEDB_190606,IEDB_2189047,IEDB_423085,IEDB_742249,IEDB_918314,IEDB_983931,SB_126,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_6,SB_7,SB_84,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1616
Gulati S, Cox A, Lewis LA, Michael FS, Li J, Boden R, Ram S, Rice PA "Enhanced factor H binding to sialylated gonococci is restricted to the sialylated lacto-N-neotetraose lipooligosaccharide species: implications for serum resistance and evidence for a bifunctional lipooligosaccharide sialyltransferase in gonococci" -
Infection and Immunity 73(11) (2005) 7390-7397
We isolated serologically identical (by serovar determination and porin variable region [VR] typing) strains of Neisseria gonorrhoeae from an infected male and two of his monogamous female sex partners. One strain (termed 398078) expressed the L1 (Gal α1→3 Gal β1→4 Glc β1→4 HepI) lipooligosaccharide (LOS) structure exclusively; the other (termed 398079) expressed the lacto-N-neotetraose (LNT; Gal β1→4 GlcNAc β1→3 Gal β1→4 Glc β1→4 HepI) LOS structure. The strain from the male index case expressed both glycoforms and exhibited both immunotypes. Nuclear magnetic resonance analysis revealed that sialic acid linked to the terminal Gal of L1 LOS via an α2→6 linkage and, as expected, to the terminal Gal of LNT LOS via an α2→3 linkage. Insertional inactivation of the sialyltransferase gene (known to sialylate LNT LOS) abrogated both L1 LOS sialylation and LNT LOS sialylation, suggesting a bifunctional nature of this enzyme in gonococci. Akin to our previous observations, sialylation of the LNT LOS of strain 398079 enhanced the binding of the complement regulatory molecule, factor H. Rather surprisingly, factor H did not bind to sialylated strain 398078. LOS sialylation conferred the LNT LOS-bearing strain complete (100%) resistance to killing by even 50% nonimmune normal human serum (NHS), whereas sialylation of L1 LOS conferred resistance only to 10% NHS. The ability of gonococcal sialylated LNT to bind factor H confers high-level serum resistance, which is not seen with sialylated L1 LOS. Thus, serum resistance mediated by sialylation of gonococcal L1 and LNT LOS occurs by different mechanisms, and specificity of factor H binding to sialylated gonococci is restricted to the LNT LOS species.
Lipooligosaccharide, enhanced, factor, sialyltransferase, binding, lacto-N-neotetraose, resistance, serum, serum resistance, species, Lewis, sialylated, implication, gonococci
NCBI PubMed ID: 16239538Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: National Research Council, Ottawa, ON K1A 0R6, Canada, Division of Infectious Diseases and Immunology, University of Massachusetts Medical School, Worcester, Massachusetts 016051, Evans Biomedical Research Center, Boston University Medical Center, Boston, Massachusetts 021183
Methods: NMR, MS
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7. Compound ID: 4315
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Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1--/rest of core-lipid A/ |
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Structure type: oligomer
Aglycon: rest of core-lipid A
Contained glycoepitopes: IEDB_130646,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_140087,IEDB_140108,IEDB_140110,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149144,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_423085,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_145,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_39,SB_6,SB_68,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 1616
Gulati S, Cox A, Lewis LA, Michael FS, Li J, Boden R, Ram S, Rice PA "Enhanced factor H binding to sialylated gonococci is restricted to the sialylated lacto-N-neotetraose lipooligosaccharide species: implications for serum resistance and evidence for a bifunctional lipooligosaccharide sialyltransferase in gonococci" -
Infection and Immunity 73(11) (2005) 7390-7397
We isolated serologically identical (by serovar determination and porin variable region [VR] typing) strains of Neisseria gonorrhoeae from an infected male and two of his monogamous female sex partners. One strain (termed 398078) expressed the L1 (Gal α1→3 Gal β1→4 Glc β1→4 HepI) lipooligosaccharide (LOS) structure exclusively; the other (termed 398079) expressed the lacto-N-neotetraose (LNT; Gal β1→4 GlcNAc β1→3 Gal β1→4 Glc β1→4 HepI) LOS structure. The strain from the male index case expressed both glycoforms and exhibited both immunotypes. Nuclear magnetic resonance analysis revealed that sialic acid linked to the terminal Gal of L1 LOS via an α2→6 linkage and, as expected, to the terminal Gal of LNT LOS via an α2→3 linkage. Insertional inactivation of the sialyltransferase gene (known to sialylate LNT LOS) abrogated both L1 LOS sialylation and LNT LOS sialylation, suggesting a bifunctional nature of this enzyme in gonococci. Akin to our previous observations, sialylation of the LNT LOS of strain 398079 enhanced the binding of the complement regulatory molecule, factor H. Rather surprisingly, factor H did not bind to sialylated strain 398078. LOS sialylation conferred the LNT LOS-bearing strain complete (100%) resistance to killing by even 50% nonimmune normal human serum (NHS), whereas sialylation of L1 LOS conferred resistance only to 10% NHS. The ability of gonococcal sialylated LNT to bind factor H confers high-level serum resistance, which is not seen with sialylated L1 LOS. Thus, serum resistance mediated by sialylation of gonococcal L1 and LNT LOS occurs by different mechanisms, and specificity of factor H binding to sialylated gonococci is restricted to the LNT LOS species.
Lipooligosaccharide, enhanced, factor, sialyltransferase, binding, lacto-N-neotetraose, resistance, serum, serum resistance, species, Lewis, sialylated, implication, gonococci
NCBI PubMed ID: 16239538Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: National Research Council, Ottawa, ON K1A 0R6, Canada, Division of Infectious Diseases and Immunology, University of Massachusetts Medical School, Worcester, Massachusetts 016051, Evans Biomedical Research Center, Boston University Medical Center, Boston, Massachusetts 021183
Methods: NMR, MS
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8. Compound ID: 4378
Structure type: monomer
Contained glycoepitopes: IEDB_136794,IEDB_146100,IEDB_149174,IEDB_423085,SB_170,SB_171,SB_172,SB_84
The structure is contained in the following publication(s):
- Article ID: 1648
Severi E, Randle G, Kivlin P, Whitfield K, Young R, Moxon R, Kelly D, Hood D, Thomas GH "Sialic acid transport in Haemophilus influenzae is essential for lipopolysaccharide sialylation and serum resistance and is dependent on a novel tripartite ATP-independent periplasmic transporter" -
Molecular Microbiology 58(4) (2005) 1173-1185
Sialylation of the lipopolysaccharide (LPS) is an important mechanism used by the human pathogen Haemophilus influenzae to evade the innate immune response of the host. We have demonstrated that N-acetylneuraminic acid (Neu5Ac or sialic acid) uptake in H. influenzae is essential for the subsequent modification of the LPS and that this uptake is mediated through a single transport system which is a member of the tripartite ATP-independent periplasmic (TRAP) transporter family. Disruption of either the siaP (HI0146) or siaQM (HI0147) genes, that encode the two subunits of this transporter, results in a complete loss of uptake of [14C]-Neu5Ac. Mutant strains lack sialylated glycoforms in their LPS and are more sensitive to killing by human serum than the parent strain. The SiaP protein has been purified and demonstrated to bind a stoichiometric amount of Neu5Ac by electrospray mass spectrometry. This binding was of high affinity with a Kd of approximately 0.1 microM as determined by protein fluorescence. The inactivation of the SiaPQM TRAP transporter also results in decreased growth of H. influenzae in a chemically defined medium containing Neu5Ac, supporting an additional nutritional role of sialic acid in H. influenzae physiology.
Lipopolysaccharide, Haemophilus, Haemophilus influenzae, LPS, gene, host, human, role, strain, acid, high, protein, response, electrospray, spectrometry, mutant, families, mass spectrometry, mechanism, modification, sialic acid, defined, biology, pathogen, purified, binding, loss, resistance, serum, serum resistance, sialylation, immune response, fluorescence, killing, N-acetylneuraminic acid, sialylated, human serum, transport, immune, Neu5Ac, electrospray mass spectrometry, medium, physiology, sensitive, transporter, inactivation, growth, affinity, uptake
NCBI PubMed ID: 16262798Journal NLM ID: 8712028Publisher: Blackwell Publishing
Institutions: Department of Biology, University of York, York, YO10 5YW, UK
Methods: genetic methods
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9. Compound ID: 5472
Structure type: oligomer
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_149174,IEDB_151531,IEDB_423085
The structure is contained in the following publication(s):
- Article ID: 2304
Vinogradov EV, Knirel YA, Shashkov AS, Paramonov NA, Kochetkov NK, Stanislavsky ES, Kholodkova EV "The structure of the O-specific polysaccharide of Salmonella arizonae O21 (Arizona 22) containing N-acetylneuraminic acid" -
Carbohydrate Research 259 (1994) 59-65
Journal NLM ID: 0043535Publisher: Elsevier
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10. Compound ID: 5621
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GroN-(2-6)-+
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GroN-(2-6)-b-D-GalpA-(1-3)-b-D-QuipNAc-(1-4)-a-D-GalpA-(1-4)-Neup5Ac |
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Structure type: oligomer
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136794,IEDB_146100,IEDB_149174,IEDB_423085,SB_170,SB_171,SB_172,SB_84
The structure is contained in the following publication(s):
- Article ID: 2436
Vinogradov EV, Holst O, Thomas-Oates JE, Broady KW, Brade H "The structure of the O-antigenic polysaccharide from lipopolysaccharide of Vibrio cholerae strain H11 (non-O1)" -
European Journal of Biochemistry 210 (1992) 491-498
After acid degradation of the lipopolysaccharide (LPS) of Vibrio cholerae strain H11 (non-O1), a tetrasaccharide was obtained, the structure of which was determined by quantitative and methylation analyses, periodate oxidation, one- and two-dimensional NMR spectroscopy, and fast-atom-bombardment and four-sector tandem mass spectrometry as β-D-GalANGro-(1-3)-β-D-QuiNAc-(1-4)-α-D-GalANGr o-(1-4)-NeuAc, in which GalANGro is N-galacturonoyl-2-aminoglycerol and QuiN 2-amino-2,6-dideoxy-glucopyranose. In addition, the trisaccharide β-D-GalANGro-(1-3)-β-D-QuiNAc-(1-4)-D-altro-hept ulose and the disaccharide α-D-GalANGro-(1-4)-NeuAc were isolated from acid-degraded lipopolysaccharide; the occurrence of sedoheptulose in lipopolysaccharide has not been described before. Based on the result of methylation analysis showing that galacturonic acid was the terminal sugar of the polysaccharide chain, and on the assumption that the tri- and the disaccharide represented the reducing and the non-reducing ends of the polysaccharide, respectively, the chemical structure of the O-specific chain of V. cholerae H11 is proposed as α-D-GalANGro-(1-4)-α-NeuAc-(2-3)-β-D-GalANGro-(1- 3)-β-D-QuiNAc- (1-[4)-α-D-GalANGro-(1-4)-α-NeuAc-(2-3)-β-D-GalANGro -(1-3)-β-D-QuiNAc-(1-]n-(1-4)-D-altro-heptulose. However, other possible structures can not be ruled out since the tri- and the disaccharide could be localised at different positions.
NCBI PubMed ID: 1281098Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Division of Biochemical Microbiology, Institut für Experimentelle Biologie und Medizin, Federal Republic of Germany
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11. Compound ID: 7254
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L-gro-a-D-manHepp-(1-2)-+
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EtN-(1-0)-?%P-?)-L-gro-a-D-manHepp-(1-3)-+ P-4)-+
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Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-D-gro-a-D-manHepp-(1-6)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-Kdop-(2--/->6) lipid A/
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EtN-(1-0)-?%P-?)-+ |
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Structure type: oligomer
Aglycon: ->6) lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130646,IEDB_130650,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_423085,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_39,SB_68,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 3277
Campagnari AA, Karalus R, Apicella M, Melaugh W, Lesse AJ, Gibson BW "Use of pyocin to select a Haemophilus ducreyi variant defective in lipooligosaccharide biosynthesis" -
Infection and Immunity 62(6) (1994) 2379-2386
Haemophilus ducreyi, a cause of genital ulcer disease in developing countries, appears to facilitate the heterosexual transmission of the human immunodeficiency virus in Africa. Despite an increase in studies of this gram-negative human pathogen, little is known about the pathogenesis of chancroid. Our studies have shown that the lipooligosaccharides (LOS) of H. ducreyi may play an important role in ulcer formation. Monoclonal antibody and mass spectrometric analyses identified a terminal trisaccharide present on H. ducreyi LOS that is immunochemically similar to human paragloboside. This epitope is present on the LOS of Neisseria gonorrhoeae, and it may be the site of attachment for pyocin lysis. We have used pyocin, produced by Pseudomonas aeruginosa, to select LOS variants with sequential saccharide deletions from N. gonorrhoeae. On the basis of the similarities between N. gonorrhoeae and H. ducreyi LOS, we employed the same technique to determine if H. ducreyi strains were susceptible to pyocin lysis. In this study, we report the generation of a pyocin N-resistant H. ducreyi strain which synthesizes a truncated version of the parental LOS. Further studies have shown that this H. ducreyi variant has lost the terminal LOS epitope defined by monoclonal antibody 3F11. This report demonstrates that H. ducreyi is sensitive to pyocins and that this technique can be used to generate H. ducreyi LOS variants. Such variants could be used in comparative studies to relate LOS structure to biologic function in the pathogenesis of chancroid.
biosynthesis, structure, Haemophilus ducreyi, Lipooligosaccharide, monoclonal antibodies, mass spectrometry, pyocin
NCBI PubMed ID: 8188362Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: AACC@Iubvms.cc.buffalo.edu
Institutions: Department of Medicine, State University of New York at Buffalo 14215.
Methods: methylation, ESI-MS, composition analysis, serological methods
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12. Compound ID: 7810
Structure type: monomer
Trivial name: 5-acetamido-5,3-dideoxy-D-glycero-β-D-galacto-oct-2-ulosonic acid
Contained glycoepitopes: IEDB_149174,IEDB_423085
The structure is contained in the following publication(s):
- Article ID: 3474
Glaze PA, Watson DC, Young NM, Tanner ME "Biosynthesis of CMP-N,N'-diacetyllegionaminic acid from UDP-N,N'-diacetylbacillosamine in Legionella pneumophila" -
Biochemistry 47(10) (2008) 3272-3282
Legionaminic acid is a nine-carbon α-keto acid that is similar in structure to other members of the sialic acid family that includes neuraminic acid and pseudaminic acid. It is found as a component of the lipopolysaccharide in several bacterial species and is perhaps best known for its presence in the O-antigen of the causative agent of Legionnaires' disease, Legionella pneumophila. In this work, the enzymes responsible for the biosynthesis and activation of N, N'-diacetyllegionaminic acid are identified for the first time. A cluster of three L. pneumophila genes bearing homology to known sialic acid biosynthetic genes (neuA,B,C) were cloned and overexpressed in Escherichia coli. The NeuC homologue was found to be a hydrolyzing UDP- N, N'-diacetylbacillosamine 2-epimerase that converts UDP- N, N'-diacetylbacillosamine into 2,4-diacetamido-2,4,6-trideoxymannose and UDP. Stereochemical and isotopic labeling studies showed that the enzyme utilizes a mechanism involving an initial anti elimination of UDP to form a glycal intermediate and a subsequent syn addition of water to generate product. This is similar to the hydrolyzing UDP- N-acetylglucosamine 2-epimerase (NeuC) of sialic acid biosynthesis, but the L. pneumophila enzyme would not accept UDP-GlcNAc as an alternate substrate. The NeuB homologue was found to be a N, N'-diacetyllegionaminic acid synthase that condenses 2,4-diacetamido-2,4,6-trideoxymannose with phosphoenolpyruvate (PEP), although the in vitro activity of the recombinant enzyme (isolated as a MalE fusion protein) was very low. The synthase activity was dependent on the presence of a divalent metal ion, and the reaction proceeded via a C-O bond cleavage process, similar to the reactions catalyzed by the sialic acid and pseudaminic acid synthases. Finally, the NeuA homologue was shown to possess the CMP- N, N'-diacetyllegionaminic acid synthetase activity that generates the activated form of legionaminic acid used in lipopolysaccharide biosynthesis. Together, the three enzymes constitute a pathway that converts a UDP-linked bacillosamine derivative into a CMP-linked legionaminic acid derivative
O-antigen, lipopolysaccharide biosynthesis, pseudaminic acid, neuraminic acid, Legionella pneumophila, legionaminic acid, Legionella, bacillosamine
NCBI PubMed ID: 18275154Journal NLM ID: 0370623Publisher: American Chemical Society
Correspondence: mtanner@chem.ubc.ca
Institutions: Department of Chemistry, University of British Columbia, Vancouver, British Columbia, Canada V6T 1Z1
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, 31P NMR, genetic methods, biochemical methods
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13. Compound ID: 8325
Structure type: oligomer
Aglycon: lipid A
Trivial name: core region
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_136794,IEDB_136906,IEDB_137472,IEDB_140529,IEDB_141794,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_151528,IEDB_167069,IEDB_190606,IEDB_423085,IEDB_983931,SB_170,SB_171,SB_172,SB_192,SB_7,SB_84
The structure is contained in the following publication(s):
- Article ID: 3622
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. II. The structure of the core region" -
Biochemistry (Moscow) 58(2) (1993) 84-99
This review summarizes data on the structure of the core of bacterial lipopolysaccharides (LPS), an oligosaccharide which binds the lipid moiety of LPS to the O-antigenic polysaccharide chain. Both S-strains with complete LPS and R-mutants having various defects of core biosynthesis are considered. The role of the core in the functioning of the outer membrane and in the manifestation of antigenic specificity of LPS is discussed.
Lipopolysaccharide, antigen, lipopolysaccharides, LPS, structure, core, bacteria, core region, region, Gram-negative bacteria, gram negative bacteria, Gram-negative, review, outer membrane, bacterial lipopolysaccharide
Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow (Russian Federation)
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14. Compound ID: 9440
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Neup5Ac-(2-3)-a-D-Galp-(1-6)-+
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-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-b-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_136044,IEDB_136794,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_1391966,IEDB_140529,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149138,IEDB_149139,IEDB_149141,IEDB_149174,IEDB_150933,IEDB_151528,IEDB_151531,IEDB_167069,IEDB_190606,IEDB_423085,IEDB_983931,SB_145,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_39,SB_6,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 4011
Deutschmann R, Boncheff AG, MacInnes JI, Monteiro MA "Discovery and characterization of a fructosylated capsule polysaccharide and sialylated lipopolysaccharide in a virulent strain of Actinobacillus suis" -
Biochemistry and Cell Biology 89(3) (2011) 325-331
We are developing a serotyping system for Actinobacillus suis based on its capsule (K) and lipopolysaccharide O-chain (O) structures. Previously, we have shown that less virulent strains of this swine pathogen express a (1→6)-β-D-glucan as both K- and O-chain polysaccharides and were serologically classified as K:1/O:1. Here, we show that representative A. suis strains with a high (H91-0380; serotype K:2/O:2) and intermediate (C84; serotype K:2/O:1) degree of virulence possess a capsule polysaccharide (K:2) composed of an O-acetylated diglycosyl phosphate repeat decorated with fructose: [→4)-3-O-Ac-β-D-GlcpNAc-(1→3)-[β-D-Fruf-(2→2)]-α-D-Galp-(1→PO(4)(-)→]. In addition, the serotype O:2 lipopolysaccharide was shown to express a sialylated O-chain [→3)-β-D-Galp-(1→4)-[Neu5Ac-(2→3)-α-D-Galp-(1→6)]-β-D-Glcp-(1→6)-β-D-GlcpNAc-(1→]. As (1→6)-β-D-glucan is ubiquitous in the environment, low levels of antibodies in the animals are predicted to prevent disease by K:1/O:1 strains. The greater potential associated with K:2/O:2 and K:2/O:1 strains is most likely due to the absence of (1→6)-β-D-glucan as the K antigen and, in the case of K:2/O:2, the presence of sialic acid in the lipopolysaccharide, a nonulosonic acid known to promote evasion of host recognition.
Lipopolysaccharide, sialic acid, fructose, capsule polysaccharide, Actinobacillus suis
NCBI PubMed ID: 21612441Publication DOI: 10.1139/o11-001Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
Correspondence: monteiro@uoguelph.ca
Institutions: Department of Chemistry, University of Guelph, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, 31P NMR, de-O-acetylation, NMR-1D, defructosylation, computational methods
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15. Compound ID: 9987
Structure type: oligomer
Compound class: LPS
Contained glycoepitopes: IEDB_136794,IEDB_136906,IEDB_137472,IEDB_140529,IEDB_141794,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_151528,IEDB_167069,IEDB_190606,IEDB_423085,IEDB_983931,SB_170,SB_171,SB_172,SB_192,SB_7,SB_84
The structure is contained in the following publication(s):
- Article ID: 4161
Krauss JH, Himmelspach K, Reuter G, Schauer R, Mayer H "Structural analysis of a novel sialic-acid-containing trisaccharide from Rhodobacter capsulatus 37b4 lipopolysaccharide" -
European Journal of Biochemistry 204 (1992) 217-223
Sialic-acid-containing lipopolysaccharides from Rhodobacter capsulatus 37b4 (S-form lipopolysaccharide), KB-1 (R-type lipopolysaccharide) and Sp 18 (deep R-type lipopolysaccharide) were investigated for the linkage and substitution of sialic acids. Methylation analysis and behaviour towards acid and enzymic hydrolysis indicated a non-reducing terminal location of sialic acids in the R-type lipopolysaccharide of strain Sp 18, whereas an internal, chain-linked location of sialic acids was found in the lipopolysaccharides of strains 37b4 and KB-1. For these latter strains, methylation analysis revealed a substitution of sialic acids by other sugars at position 7 for strain 37b4 and positions 4 and 7 for strain KB-1. In accordance with the chain-linked position of sialic acids, mild hydrolysis of R. capsulatus 37b4 lipopolysaccharide with acetic acid released a trisaccharide with sialic acid at the reducing terminus. Structural investigation of this trisaccharide by methylation analysis, 1H- and 13C-NMR spectroscopy revealed the presence of the disaccharide Gal1-6Glc at the non-reducing end, probably with an α-anomeric configuration of the galactose residue, i.e. melibiose, beta-glycosidically linked to position 7 of sialic acid. Therefore the structure Gal α 1-6Glc β 1-7Neu5Ac is proposed for this core oligosaccharide from R. capsulatus 37b4 lipopolysaccharide.
NCBI PubMed ID: 1310942Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Max-Planck-Institut für Immunbiologie, Freiburg, Federal Republic of Germany
Methods: 13C NMR, 1H NMR
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