Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: gastroenteritis [ICD11:
1A40.0 
];
infection due to Campylobacter jejuni [ICD11:
XN4Q5 ]
The structure was elucidated in this paperNCBI PubMed ID: 21257763Publication DOI: 10.1074/jbc.M110.181750Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: michel.gilbert
nrc-cnrc.gc.ca
Institutions: From the Institute for Biological Sciences, National Research Council, Ottawa, Ontario K1A 0R6, Canada
Campylobacter jejuni is well known for synthesizing ganglioside mimics within the glycan component of its lipooligosaccharide (LOS), which have been implicated in triggering Guillain-Barre syndrome. We now confirm that this pathogen is capable of synthesizing a much broader spectrum of host glycolipid/glycoprotein mimics within its LOS. P blood group and paragloboside (lacto-N-neotetraose) antigen mimicry is exhibited by RM1221, a strain isolated from a poultry source. RM1503, a gastroenteritis-associated strain, expresses lacto-N-biose and sialyl-Lewis c units, the latter known as the pancreatic tumor-associated antigen, DU-PAN-2 (or LSTa). C. jejuni GC149, a Guillain-Barre syndrome-associated strain, expresses an unusual sialic acid-containing hybrid oligosaccharide with similarity to both ganglio and P(k) antigens and can, through phase variation of its LOS biosynthesis genes, display GT1a or GD3 ganglioside mimics. We show that the sialyltransferase CstII and the galactosyltransferase CgtD are involved in the synthesis of multiple mimic types, with LOS structural diversity achieved through evolving allelic substrate specificity.
Lipooligosaccharide, Campylobacter jejuni, gangliosides, mimicry
Structure type: oligomer
Location inside paper: table S8
Aglycon: phenylthio
Trivial name: Gal-GM1a oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_130651,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_144987,IEDB_146100,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_151528,IEDB_1625329,IEDB_190606,IEDB_742247,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_195,SB_23,SB_24,SB_25,SB_31,SB_39,SB_62,SB_68,SB_7,SB_8,SB_84,SB_88,SB_96
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, sugar analysis, 31P NMR, NMR-1D, genetic methods, de-N-O-acylation, LC-MS, CE
Biosynthesis and genetic data: genetic data, substrate specificity of CgtD and CstII
Synthetic data: chemoenzymatic
Comments, role: Chemoenzymaticcally synthesized Gal-GM1a oligosaccharide (thio-phenyl derivative).
Related record ID(s): 26226, 26647, 26648, 26649, 26650
NCBI Taxonomy refs (TaxIDs): 197
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9
4,3,5 Ac
4,3 aXNeup ? ? 38.0 69.9 52.7 74.3 69.2 73.4 64.0
4,4,3,4 aDGalp 101.6 69.9 70.4 70.2 72.0 61.7
4,4,3 bDGalp 106.1 71.9 73.4 78.7 76.2 ?
4,4,2 Ac
4,4 bDGalpN 103.6 52.4 81.5 69.2 75.6 ?
4 bDGalp 103.7 71.2 75.6 78.4 75.3 ?
bDGlcp1S 88.3 72.6 77.0 79.4 79.9 61.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9
4,3,5 Ac
4,3 aXNeup - - 1.91-2.67 3.77 3.81 3.49 3.60 3.74 3.62-3.87
4,4,3,4 aDGalp 4.96 3.82 3.91 4.03 4.36 3.69-3.71
4,4,3 bDGalp 4.62 3.56 3.71 4.04 3.77 ?
4,4,2 Ac
4,4 bDGalpN 4.78 4.06 3.83 4.12 3.73 ?
4 bDGalp 4.53 3.36 4.15 4.13 3.76 ?
bDGlcp1S 4.84 3.40 3.69 3.65 3.63 3.80-3.97
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9
4,3,5 Ac
4,3 aXNeup 38.0/1.91-2.67 69.9/3.77 52.7/3.81 74.3/3.49 69.2/3.60 73.4/3.74 64.0/3.62-3.87
4,4,3,4 aDGalp 101.6/4.96 69.9/3.82 70.4/3.91 70.2/4.03 72.0/4.36 61.7/3.69-3.71
4,4,3 bDGalp 106.1/4.62 71.9/3.56 73.4/3.71 78.7/4.04 76.2/3.77 ?/?
4,4,2 Ac
4,4 bDGalpN 103.6/4.78 52.4/4.06 81.5/3.83 69.2/4.12 75.6/3.73 ?/?
4 bDGalp 103.7/4.53 71.2/3.36 75.6/4.15 78.4/4.13 75.3/3.76 ?/?
bDGlcp1S 88.3/4.84 72.6/3.40 77.0/3.69 79.4/3.65 79.9/3.63 61.3/3.80-3.97
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 |
|---|
| 4,3,5 | Ac | |
| 4,3 | aXNeup |
|
| 1.91
2.67 | 3.77 | 3.81 | 3.49 | 3.60 | 3.74 | 3.62
3.87 |
| 4,4,3,4 | aDGalp | 4.96 | 3.82 | 3.91 | 4.03 | 4.36 | 3.69
3.71 | |
| 4,4,3 | bDGalp | 4.62 | 3.56 | 3.71 | 4.04 | 3.77 | ? | |
| 4,4,2 | Ac | |
| 4,4 | bDGalpN | 4.78 | 4.06 | 3.83 | 4.12 | 3.73 | ? | |
| 4 | bDGalp | 4.53 | 3.36 | 4.15 | 4.13 | 3.76 | ? | |
| | bDGlcp1S | 4.84 | 3.40 | 3.69 | 3.65 | 3.63 | 3.80
3.97 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 |
|---|
| 4,3,5 | Ac | |
| 4,3 | aXNeup | ? | ? | 38.0 | 69.9 | 52.7 | 74.3 | 69.2 | 73.4 | 64.0 |
| 4,4,3,4 | aDGalp | 101.6 | 69.9 | 70.4 | 70.2 | 72.0 | 61.7 | |
| 4,4,3 | bDGalp | 106.1 | 71.9 | 73.4 | 78.7 | 76.2 | ? | |
| 4,4,2 | Ac | |
| 4,4 | bDGalpN | 103.6 | 52.4 | 81.5 | 69.2 | 75.6 | ? | |
| 4 | bDGalp | 103.7 | 71.2 | 75.6 | 78.4 | 75.3 | ? | |
| | bDGlcp1S | 88.3 | 72.6 | 77.0 | 79.4 | 79.9 | 61.3 | |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":38,"l":"3","c":[0,0,225]},{"s":69.9,"l":"4","c":[0,0,225]},{"s":52.7,"l":"5","c":[0,0,225]},{"s":74.3,"l":"6","c":[0,0,225]},{"s":69.2,"l":"7","c":[0,0,225]},{"s":73.4,"l":"8","c":[0,0,225]},{"s":64,"l":"9","c":[0,0,225]},{"s":101.6,"l":"1","c":[230,0,30]},{"s":69.9,"l":"2","c":[230,0,30]},{"s":70.4,"l":"3","c":[230,0,30]},{"s":70.2,"l":"4","c":[230,0,30]},{"s":72,"l":"5","c":[230,0,30]},{"s":61.7,"l":"6","c":[230,0,30]},{"s":106.1,"l":"1","c":[0,165,0]},{"s":71.9,"l":"2","c":[0,165,0]},{"s":73.4,"l":"3","c":[0,165,0]},{"s":78.7,"l":"4","c":[0,165,0]},{"s":76.2,"l":"5","c":[0,165,0]},{"s":103.6,"l":"1","c":[120,0,225]},{"s":52.4,"l":"2","c":[120,0,225]},{"s":81.5,"l":"3","c":[120,0,225]},{"s":69.2,"l":"4","c":[120,0,225]},{"s":75.6,"l":"5","c":[120,0,225]},{"s":103.7,"l":"1","c":[0,192,255]},{"s":71.2,"l":"2","c":[0,192,255]},{"s":75.6,"l":"3","c":[0,192,255]},{"s":78.4,"l":"4","c":[0,192,255]},{"s":75.3,"l":"5","c":[0,192,255]},{"s":88.3,"l":"1","c":[220,0,180]},{"s":72.6,"l":"2","c":[220,0,180]},{"s":77,"l":"3","c":[220,0,180]},{"s":79.4,"l":"4","c":[220,0,180]},{"s":79.9,"l":"5","c":[220,0,180]},{"s":61.3,"l":"6","c":[220,0,180]}])
The spectrum also has 5 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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Found 1 record.
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