Found 9 structures.
Displayed structures from 1 to 9
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1. Compound ID: 1116
a-Neup5Ac-(2-8)-a-Neup5Ac-(2-3)-+
|
a-Neup5Ac-(2-8)-a-Neup5Ac-(2-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Gal-(1-4)-b-D-Glcp-(1-?)-CER |
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Structure type: oligomer
Trivial name: GQ1b
Compound class: ganglioside
Contained glycoepitopes: IEDB_130648,IEDB_130675,IEDB_130676,IEDB_130678,IEDB_130679,IEDB_130680,IEDB_130681,IEDB_130683,IEDB_130684,IEDB_130686,IEDB_134627,IEDB_136044,IEDB_136095,IEDB_136794,IEDB_137339,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_150937,IEDB_153198,IEDB_153199,IEDB_190606,IEDB_433718,IEDB_547903,IEDB_858580,IEDB_983931,SB_116,SB_13,SB_14,SB_144,SB_164,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_2,SB_22,SB_23,SB_24,SB_25,SB_28,SB_3,SB_35,SB_37,SB_38,SB_39,SB_4,SB_41,SB_42,SB_5,SB_6,SB_68,SB_7,SB_70,SB_71,SB_76,SB_8,SB_84,SB_88,SB_94,SB_95,SB_96,SB_97,SB_98
The structure is contained in the following publication(s):
- Article ID: 335
Neisser A, Bernheimer H, Berger T, Moran AP, Schwerer B "Serum antibodies against gangliosides and Campylobacter jejuni lipopolysaccharides in Miller-Fisher syndrome" -
Infection and Immunity 65(10) (1997) 4038-4042
Seven patients with Miller Fisher syndrome (MFS), six in the acute phase and one in the recovery phase, were investigated for serum antibodies against gangliosides and purified lipopolysaccharides (LPS) from different strains of Campylobacter jejuni, including the MFS-associated serotypes O:2 and O:23. Immunoglobulin G antibodies against gangliosides GT1a and GQ1b were found in five of six patients in the acute phase of disease. Three of these patients also displayed antibodies to ganglioside GD2, a finding not previously reported for MFS. All anti-GT1a- and anti-GQ1b-seropositive patients showed antibody binding to C. jejuni LPS, predominantly to O:2 and O:23 LPS. Antibody cross-reactivity between gangliosides GT1a and GQ1b and O:2 and O:23 LPS was demonstrated by adsorption studies. This cross-reactivity between gangliosides and C.jejuni LPS, which is obviously due to oligosaccharide homologies, may be an important pathogenetic factor in the development of MFS after C. jejuni infection
lipopolysaccharides, antibodies, Campylobacter, Campylobacter jejuni, gangliosides, Miller-Fisher syndrome
NCBI PubMed ID: 9317004Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: andrea.neisser@univie.ac.at
Institutions: Institute of Neurology and Department of Neurology, University of Vienna, Vienna, Austria, Department of Microbiology, University College, Galway, Ireland
Methods: serological methods, TLC-immunostaining
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2. Compound ID: 1117
a-Neup5Ac-(2-3)-+
|
a-Neup5Ac-(2-8)-a-Neup5Ac-(2-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Gal-(1-4)-b-D-Glcp-(1-?)-CER |
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Structure type: oligomer
Trivial name: GT1b
Compound class: ganglioside
Contained glycoepitopes: IEDB_130648,IEDB_130678,IEDB_130679,IEDB_130683,IEDB_130686,IEDB_134627,IEDB_136044,IEDB_136095,IEDB_136794,IEDB_137339,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_150937,IEDB_153198,IEDB_153199,IEDB_190606,IEDB_547903,IEDB_983931,SB_116,SB_13,SB_144,SB_164,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_2,SB_22,SB_23,SB_24,SB_25,SB_3,SB_35,SB_37,SB_39,SB_4,SB_41,SB_42,SB_5,SB_6,SB_68,SB_7,SB_70,SB_71,SB_76,SB_8,SB_84,SB_88,SB_96,SB_97,SB_98
The structure is contained in the following publication(s):
- Article ID: 335
Neisser A, Bernheimer H, Berger T, Moran AP, Schwerer B "Serum antibodies against gangliosides and Campylobacter jejuni lipopolysaccharides in Miller-Fisher syndrome" -
Infection and Immunity 65(10) (1997) 4038-4042
Seven patients with Miller Fisher syndrome (MFS), six in the acute phase and one in the recovery phase, were investigated for serum antibodies against gangliosides and purified lipopolysaccharides (LPS) from different strains of Campylobacter jejuni, including the MFS-associated serotypes O:2 and O:23. Immunoglobulin G antibodies against gangliosides GT1a and GQ1b were found in five of six patients in the acute phase of disease. Three of these patients also displayed antibodies to ganglioside GD2, a finding not previously reported for MFS. All anti-GT1a- and anti-GQ1b-seropositive patients showed antibody binding to C. jejuni LPS, predominantly to O:2 and O:23 LPS. Antibody cross-reactivity between gangliosides GT1a and GQ1b and O:2 and O:23 LPS was demonstrated by adsorption studies. This cross-reactivity between gangliosides and C.jejuni LPS, which is obviously due to oligosaccharide homologies, may be an important pathogenetic factor in the development of MFS after C. jejuni infection
lipopolysaccharides, antibodies, Campylobacter, Campylobacter jejuni, gangliosides, Miller-Fisher syndrome
NCBI PubMed ID: 9317004Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: andrea.neisser@univie.ac.at
Institutions: Institute of Neurology and Department of Neurology, University of Vienna, Vienna, Austria, Department of Microbiology, University College, Galway, Ireland
Methods: serological methods, TLC-immunostaining
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3. Compound ID: 4470
a-Neup5Ac-(2-8)-a-Neup5Ac-(2-3)-+
|
a-Neup5Ac-(2-8)-a-Neup5Ac-(2-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-?)-CER-(?--/Ceramide/ |
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Structure type: oligomer
Aglycon: Ceramide
Trivial name: GQ1b
Compound class: ganglioside
Contained glycoepitopes: IEDB_130648,IEDB_130675,IEDB_130676,IEDB_130678,IEDB_130679,IEDB_130680,IEDB_130681,IEDB_130683,IEDB_130684,IEDB_130686,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137339,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_150937,IEDB_153198,IEDB_153199,IEDB_190606,IEDB_433718,IEDB_547903,IEDB_858580,IEDB_983931,SB_116,SB_13,SB_14,SB_144,SB_164,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_2,SB_22,SB_23,SB_24,SB_25,SB_28,SB_3,SB_35,SB_37,SB_38,SB_39,SB_4,SB_41,SB_42,SB_5,SB_6,SB_68,SB_7,SB_70,SB_71,SB_76,SB_8,SB_84,SB_88,SB_94,SB_95,SB_96,SB_97,SB_98
The structure is contained in the following publication(s):
- Article ID: 1689
Jacobs BC, Endtz HP, van der Meche FGA, Hazenberg MP, Achtereekte HAM, Van Doorn PA "Serum anti-GQ1b IgG antibodies recognize surface epitopes on Campylobacter jejuni from patients with Miller Fisher syndrome" -
Annals of Neurology 37 (1995) 260-264
Three patients who had diarrhea prior to the development of Miller Fisher syndrome are presented. Campylobacter jejuni was isolated from stool specimens from all patients. High titers of anti-GQ1b IgG antibodies were demonstrated in the serum of these patients by enzyme-linked immunosorbent assay and thin-layer chromatography overlay. In enzyme-linked immunosorbent assay inhibition studies the anti-GQ1b IgG antibodies bound specifically to whole bacteria of the Miller Fisher syndrome-associated C. jejuni strains. The presence of anti-GQ1b IgG binding epitopes on the surface of the C. jejuni from the patients was not exclusively associated with a specific Penner serotype. It is suggested that anti-GQ1b antibodies are formed during the initial infection that elicits Miller Fisher syndrome. The cross-reactivity of anti-GQ1b IgG antibodies with surface epitopes on Miller Fisher syndrome-associated C. jejuni strains supports the hypothesis of molecular mimicry between bacteria and neural tissue.
NCBI PubMed ID: 7531419Journal NLM ID: 7707449Institutions: Department of Neurology, University Hospital Dijkzigt, The Netherlands
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4. Compound ID: 5797
a-Neup5Ac-(2-3)-+
|
b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-?)-CER-(?--/Ceramide/ |
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Structure type: oligomer
Aglycon: Ceramide
Trivial name: GM1
Compound class: ganglioside
Contained glycoepitopes: IEDB_130648,IEDB_130678,IEDB_130679,IEDB_130683,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137339,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_190606,IEDB_547903,IEDB_983931,SB_116,SB_13,SB_144,SB_164,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_2,SB_23,SB_24,SB_25,SB_3,SB_37,SB_39,SB_4,SB_41,SB_5,SB_6,SB_68,SB_7,SB_71,SB_76,SB_8,SB_84,SB_88,SB_96
The structure is contained in the following publication(s):
- Article ID: 1303
Yuki N, Handa S, Tai T, Takahashi M, Saito K, Tsujino Y, Taki T "Ganglioside-like epitopes of lipopolysaccharides from Campylobacter jejuni (PEN 19) in three isolates from patients with Guillain-Barré syndrome" -
Journal of the Neurological Sciences 130 (1995) 112-116
Sera from patients with Guillain-Barre syndrome (GBS) frequently have anti-GM1 antibody. We earlier showed that an lipopolysaccharides (LPS) from Campylobacter jejuni (PEN 19) isolated from a GBS patient has a GM1 ganglioside-like structure. Aspinall et al. (Biochemistry,61 (1994) 335-337) reported that OH 4382 has an LPS that bears a CD3 ganglioside-like structure and that OH 4384 has an LPS that bears a GT1a-like structure; both strains were isolated from patients with GBS. They also suggested a GM1-like structure is present in the LPSs from OH 4384, but failed to show the presence in the LPSs from OH 4382. To clarify the pathogenesis of GBS after infection by C. jejuni (PEN 19), we investigated the carbohydrate structures of the three strains by thin-layer chromatography immunostaining with cholera toxin and monoclonal anti-ganglioside antibodies. We found that both OH 4382 and OH 4384 have an LPS with the GM1 epitope as well as one with the GT1a or GD3 epitope.
Lipopolysaccharide, lipopolysaccharides, LPS, isolate, epitope, Campylobacter, Campylobacter jejuni, ganglioside, mimicry, syndrome, epitopes
NCBI PubMed ID: 7544402Journal NLM ID: 0375403Publisher: Elsevier
Institutions: Department of Biochemistry, Faculty of Medicine, Tokyo Medical and Dental University, 1-5-45 Yushima, Bunkyo-ku, Tokyo113, Japan, Department of Tumor Immunology, Tokyo Metropolitan Institute of Medical Science, Bunkyo-ku, Tokyo, Japan, Department of Microbiology, Tokyo Metropolitan Research Laboratory of Public Health, Shinjuku-ku, Tokyo, Japan, Department of Pediatrics, Ohtemae Hospital, Chuo-ku, Osaka, Japan
Methods: NMR-2D, NMR
- Article ID: 2545
Barbieri CL, Giorgio S, Merjan AJC, Figueiredo EN "Glycosphingolipid antigens of Leishmania (Leishmania) amazonensisamastigotes identified by use of a monoclonal antibody" -
Infection and Immunity 61 (1993) 2131-2137
Journal NLM ID: 0246127Publisher: American Society for Microbiology
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5. Compound ID: 5798
a-Neup5Ac-(2-3)-+
|
a-Neup5Ac-(2-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-?)-CER-(?--/Ceramide/ |
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Structure type: oligomer
Aglycon: Ceramide
Trivial name: GD1a
Compound class: ganglioside
Contained glycoepitopes: IEDB_130648,IEDB_130678,IEDB_130679,IEDB_130683,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137339,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_190606,IEDB_547903,IEDB_983931,SB_116,SB_13,SB_144,SB_164,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_2,SB_22,SB_23,SB_24,SB_25,SB_3,SB_37,SB_39,SB_4,SB_41,SB_5,SB_6,SB_68,SB_7,SB_70,SB_71,SB_76,SB_8,SB_84,SB_88,SB_96,SB_97,SB_98
The structure is contained in the following publication(s):
- Article ID: 2545
Barbieri CL, Giorgio S, Merjan AJC, Figueiredo EN "Glycosphingolipid antigens of Leishmania (Leishmania) amazonensisamastigotes identified by use of a monoclonal antibody" -
Infection and Immunity 61 (1993) 2131-2137
Journal NLM ID: 0246127Publisher: American Society for Microbiology
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6. Compound ID: 6114
a-Neup5Ac-(2-3)-+
|
a-Neup5Ac-(2-8)-a-Neup5Ac-(2-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-?)-CER-(?--/Ceramide/ |
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Structure type: oligomer
Aglycon: Ceramide
Trivial name: GT1a
Compound class: ganglioside
Contained glycoepitopes: IEDB_130648,IEDB_130678,IEDB_130679,IEDB_130683,IEDB_130686,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137339,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_150937,IEDB_153198,IEDB_153199,IEDB_190606,IEDB_547903,IEDB_983931,SB_116,SB_13,SB_144,SB_164,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_2,SB_22,SB_23,SB_24,SB_25,SB_3,SB_35,SB_37,SB_39,SB_4,SB_41,SB_42,SB_5,SB_6,SB_68,SB_7,SB_70,SB_71,SB_76,SB_8,SB_84,SB_88,SB_96,SB_97,SB_98
The structure is contained in the following publication(s):
- Article ID: 1303
Yuki N, Handa S, Tai T, Takahashi M, Saito K, Tsujino Y, Taki T "Ganglioside-like epitopes of lipopolysaccharides from Campylobacter jejuni (PEN 19) in three isolates from patients with Guillain-Barré syndrome" -
Journal of the Neurological Sciences 130 (1995) 112-116
Sera from patients with Guillain-Barre syndrome (GBS) frequently have anti-GM1 antibody. We earlier showed that an lipopolysaccharides (LPS) from Campylobacter jejuni (PEN 19) isolated from a GBS patient has a GM1 ganglioside-like structure. Aspinall et al. (Biochemistry,61 (1994) 335-337) reported that OH 4382 has an LPS that bears a CD3 ganglioside-like structure and that OH 4384 has an LPS that bears a GT1a-like structure; both strains were isolated from patients with GBS. They also suggested a GM1-like structure is present in the LPSs from OH 4384, but failed to show the presence in the LPSs from OH 4382. To clarify the pathogenesis of GBS after infection by C. jejuni (PEN 19), we investigated the carbohydrate structures of the three strains by thin-layer chromatography immunostaining with cholera toxin and monoclonal anti-ganglioside antibodies. We found that both OH 4382 and OH 4384 have an LPS with the GM1 epitope as well as one with the GT1a or GD3 epitope.
Lipopolysaccharide, lipopolysaccharides, LPS, isolate, epitope, Campylobacter, Campylobacter jejuni, ganglioside, mimicry, syndrome, epitopes
NCBI PubMed ID: 7544402Journal NLM ID: 0375403Publisher: Elsevier
Institutions: Department of Biochemistry, Faculty of Medicine, Tokyo Medical and Dental University, 1-5-45 Yushima, Bunkyo-ku, Tokyo113, Japan, Department of Tumor Immunology, Tokyo Metropolitan Institute of Medical Science, Bunkyo-ku, Tokyo, Japan, Department of Microbiology, Tokyo Metropolitan Research Laboratory of Public Health, Shinjuku-ku, Tokyo, Japan, Department of Pediatrics, Ohtemae Hospital, Chuo-ku, Osaka, Japan
Methods: NMR-2D, NMR
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7. Compound ID: 8377
a-Neup5Ac-(2-3)-+
|
b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-1)-CER-(?--/ceramide/ |
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Structure type: oligomer
Aglycon: ceramide
Trivial name: GM1
Compound class: ganglioside
Contained glycoepitopes: IEDB_130648,IEDB_130678,IEDB_130679,IEDB_130683,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137339,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_190606,IEDB_547903,IEDB_983931,SB_116,SB_13,SB_144,SB_164,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_2,SB_23,SB_24,SB_25,SB_3,SB_37,SB_39,SB_4,SB_41,SB_5,SB_6,SB_68,SB_7,SB_71,SB_76,SB_8,SB_84,SB_88,SB_96
The structure is contained in the following publication(s):
- Article ID: 3646
Komagamine T, Yuki N "Ganglioside mimicry as a cause of Guillain-Barre syndrome" -
CNS and Neurological Disorders Drug Targets 5(4) (2006) 391-400
Guillain-Barre syndrome (GBS), characterized by acute progressive limb weakness and areflexia, is the prototype of postinfectious autoimmune diseases. Campylobacter jejuni is the most frequently identified agent of infection in GBS patients, often preceding acute motor axonal neuropathy (AMAN), a variant of GBS. Anti-GM1, anti-GM1b, anti-GD1a, and anti-GalNAc-GD1a IgG antibodies are associated with AMAN. Carbohydrate mimicry [Galβ1-3GalNAcβ1-4(NeuAcα2-3)Galβ1-] was seen between the lipo-oligosaccharide of C. jejuni isolated from an AMAN patient and human GM1 ganglioside. Sensitization with the lipo-oligosaccharide of C. jejuni induces AMAN in rabbits as does sensitization with GM1 ganglioside. Paralyzed rabbits have pathological changes in their peripheral nerves identical to changes seen in human GBS. C. jejuni infection may induce anti-ganglioside antibodies by molecular mimicry, eliciting AMAN. This is the first verification of the causative mechanism of molecular mimicry in an autoimmune disease. To express ganglioside mimics, C. jejuni requires specific gene combinations that function in sialic acid biosynthesis or transfer. The knockout mutants of these landmark genes of GBS show reduced reactivity with GBS patients' sera, and fail to induce an anti-ganglioside antibody response in mice. These genes are crucial for the induction of neuropathogenic cross-reactive antibodies. An approach for evaluating intravenous immune globulin, a treatment for GBS, based on our animal model of AMAN is also discussed in this review, and recent advances made in this field are described.
Campylobacter jejuni, ganglioside, Guillain-Barre syndrome, molecular mimicry, Autoimmune disease
NCBI PubMed ID: 16918391Journal NLM ID: 101269155Publisher: Bentham Science Publishers
Correspondence: yuki@dokkyomed.ac.jp
Institutions: Department of Neurology and Research Institute for Neuroimmunological Diseases, Dokkyo Medical University School of Medicine, Tochigi, Japan
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8. Compound ID: 10897
a-Neup5Ac-(2-8)-a-Neup5Ac-(2-3)-+
|
a-Neup5Ac-(2-3)-b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-1)-CER |
Show graphically |
Structure type: structural motif or average structure
Trivial name: trisialoganglioside
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_130676,IEDB_130678,IEDB_130679,IEDB_130680,IEDB_130681,IEDB_130683,IEDB_130684,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137339,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_150937,IEDB_153198,IEDB_153199,IEDB_190606,IEDB_433718,IEDB_547903,IEDB_858580,IEDB_983931,SB_116,SB_13,SB_14,SB_144,SB_164,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_2,SB_22,SB_23,SB_24,SB_25,SB_28,SB_3,SB_35,SB_37,SB_39,SB_4,SB_41,SB_42,SB_5,SB_6,SB_68,SB_7,SB_70,SB_71,SB_76,SB_8,SB_84,SB_88,SB_94,SB_95,SB_96,SB_97,SB_98
The structure is contained in the following publication(s):
- Article ID: 4430
Ovodov YS "Bacterial capsular antigens. Structural patterns of capsular antigens" -
Biochemistry (Moscow) 71(9) (2006) 937-954
Structural patterns of bacterial capsular antigens including capsular polysaccharides and exoglycans are given in this review. In addition, the immunological activity of capsular antigens and their role in type specificity of bacteria are discussed.
structure, capsular polysaccharides, bacterial capsular antigens, bacterial exoglycans, immunological activity, type specificity
NCBI PubMed ID: 17009947Publication DOI: 10.1134/S000629790609001XJournal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: ovoys@physiol.komisc.ru
Institutions: Institute of Physiology, Komi Science Center, Urals Branch of the Russian Academy of Sciences, Syktyvkar 167982, Russia
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9. Compound ID: 14000
a-Neup5Ac-(2-3)-+
|
b-D-Galp-(1-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-?)-CER |
Show graphically |
Structure type: oligomer
Trivial name: GM1
Compound class: ganglioside
Contained glycoepitopes: IEDB_130648,IEDB_130678,IEDB_130679,IEDB_130683,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137339,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_190606,IEDB_547903,IEDB_983931,SB_116,SB_13,SB_144,SB_164,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_2,SB_23,SB_24,SB_25,SB_3,SB_37,SB_39,SB_4,SB_41,SB_5,SB_6,SB_68,SB_7,SB_71,SB_76,SB_8,SB_84,SB_88,SB_96
The structure is contained in the following publication(s):
- Article ID: 5525
Yoshida F, Yoshinaka H, Tanaka H, Hanashima S, Yamaguchi Y, Ishihara M, Saburomaru M, Karo Y, Saito R, Ando H, Kiso M, Imamura A, Ishida H "Synthesis of the Core Oligosaccharides of Lipooligosaccharides from Campylobacter jejuni: A Putative Cause of Guillain-Barré Syndrome" -
Chemistry: a European Journal 25(3) (2019) 796-805
The chemical synthesis of the highly branched core oligosaccharides of lipooligosaccharides (LOSs) found in Campylobacter jejuni, which causes Guillain-Barré syndrome by a preceding infection, is described. The target LOS mimics, consisting of eight or nine monosaccharides, were classified into three groups as key building blocks: ganglioside-core tetra-/pentasaccharides (GM1-/GD1a-like), l-glycero-d-manno-heptose-containing trisaccharides, and 3-deoxy-d-manno-2-octulosonic acid (KDO) residues. These synthetic fragments were obtained from commercially available monosaccharides. Less obtainable l-glycero-d-manno-heptose and KDO residues, as key components of the LOSs, were synthesized from p-methoxyphenyl d-mannoside and di-O-isopropylidene-protected d-mannose, respectively. The synthesis of α-KDO glycoside, as one of the most difficult stereocontrolled glycosidic constructions, was achieved by treating a 2,3-ene derivative of KDO with phenylselenyl trifluoromethanesulfonate as a suitable alpha-directing reagent. All synthetic blocks were constructed through a convergent synthetic route, which resulted in the first synthesis of structurally challenging LOS core glycans containing ganglioside GM1 and GD1a-core sequences.
chemistry, structural, group, Research, gangliosides, Guillain-Barre syndrome, cluster, lipooligosaccharides, glycosylation, PDF, Science, glycobiology, arbohydrates
NCBI PubMed ID: 30351481Publication DOI: 10.1002/chem.201804862Journal NLM ID: 9513783Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
Correspondence: Akihiro Imamura
; Hideharu Ishida
Institutions: Department of Applied Bio-organic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu, 501-1193, Japan, Center for Highly Advanced Integration and Nano and Life Sciences, (G-CHAIN), Gifu University, 1-1 Yanagido, Gifu-shi, Gifu, 501-1193, Japan, Structural Glycobiology Team, Systems Glycobiology Research Group, RIKEN Global Research Cluster, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, UV, glycosylation, optical rotation measurement, ESI-TOF-MS, flash chromatography
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