Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Campylobacter jejuni [ICD11: XN4Q5 ]
 
The structure was elucidated in this paper
NCBI PubMed ID: 12392544
Publication DOI: 10.1046/j.1432-1033.2002.03201.x
Journal NLM ID: 0107600
Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: jean-robert.brissonnrc.ca; Monteimwyeth.com
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Canada, Wyeth Vaccines Research, 211 Bailey Road, West Henrietta, NY, 14586, USA

Campylobacter jejuni infections are one of the leading causes of human gastroenteritis and are suspected of being a precursor to Guillain- Barre and Miller-Fisher syndromes. Recently, the complete genome sequence of C. jejuni NCTC11168 was described. In this study, the molecular structure of the lipooligosaccharide and capsular polysaccharide of C. jejuni NCTC11168 was investigated. The lipooligosaccharide was shown to exhibit carbohydrate structures analogous to the GM1a and GM2 carbohydrate epitopes of human gangliosides (shown below): The high Mr capsule polysaccharide was composed of β-D-Ribp, β-D-GalfNAc, α-D-GlcpA6(NGro), a uronic acid amidated with 2-amino-2-deoxyglycerol at C-6, and 6-O-methyl-d-glycero-α-l-gluco-heptopyranose as a side-branch (shown below):

. The structural information presented here will aid in the identification and characterization of specific enzymes that are involved in the biosynthesis of these structures and may lead to the discovery of potential therapeutic targets. In addition, the correlation of carbohydrate structure with gene complement will aid in the elucidation of the role of these surface carbohydrates in C. jejuni pathogenesis.

structure, Lipooligosaccharide, human, strain, capsular, polysaccharide, carbohydrate, molecular, Molecular Structure, acid, epitope, capsular polysaccharide, Campylobacter, Campylobacter jejuni, ganglioside, gangliosides, high, infection, syndrome, epitopes, uronic acid, precursor, sequence, capsule, genome, capsule polysaccharide, Miller-Fisher syndrome, Miller Fisher syndrome, carbohydrate structure

Structure type: oligomer
Location inside paper: Fig.3 GM2
Trivial name: GM2
Compound class: LOS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_131186,IEDB_135818,IEDB_136044,IEDB_136794,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150933,IEDB_151528,IEDB_167072,IEDB_190606,IEDB_2189047,IEDB_742245,IEDB_983931,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_25,SB_39,SB_68,SB_7,SB_84,SB_88
 
Methods: NMR, Smith degradation
Comments, role: substitution with ethanolamine is partial, analogous structure to GM2 carbohydrate epitope of human ganglioside
 
Related record ID(s): 3434, 3507, 3610, 3611, 3612, 3613
NCBI Taxonomy refs (TaxIDs): 197
Reference(s) to other database(s): GTC:G71859DF
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There are 2 chemically distinct structures. Please, select:
bDGlcp(1-2)[aDGalp(1-2)[Ac(1-5)aXNeup(2-3)[Ac(1-2)bDGalpN(1-4)]bDGalp(1-3)]bDGalp(1-3)]aXLDmanHepp(1-3)[%xXEt?N(1-P-6),bDGlcp(1-4)]aXLDmanHepp(1-5)?XKdop bDGlcp(1-2)[aDGalp(1-2)[Ac(1-5)aXNeup(2-3)[Ac(1-2)bDGalpN(1-4)]bDGalp(1-3)]bDGalp(1-3)]aXLDmanHepp(1-3)[%xXEt?N(1-P-6),bDGlcp(1-4)]aXLDmanHepp(1-5)xXKdoa

SVGMWSMILES3D molIonize

 

CC(=O)N[C@H]1[C@H](O[C@@H]2[C@H](O[C@]3(C(=O)O)C[C@H](O)[C@@H](NC(C)=O)[C@H]([C@H](O)[C@H](O)CO)O3)[C@@H](O)[C@H](O[C@H]3[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]4[C@H](O)[C@@H]([C@@H](O)CO)O[C@H](O[C@@H]5[C@H](O)[C@@H](O[C@H]6[C@@H]([C@H](O)CO)OC(O)(C(=O)O)C[C@H]6O)O[C@H]([C@H](CO)OP(=O)(O)OCCN)[C@H]5O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@H]4O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H]3O[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)O[C@@H]2CO)O[C@H](CO)[C@H](O)[C@@H]1O

2050.729 g/mol (C₇₃H₁₂₄N₃O₆₁P)

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