Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: diarrhea [ICD11:
ME05.1 
, ICD11:
SA55 ];
autism spectrum disorder (ASD) [ICD11:
6A02 ]
The structure was elucidated in this paperNCBI PubMed ID: 37023666Publication DOI: 10.1016/j.carres.2023.108805Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: T.L. Lowary <tlowary
gate.sinica.edu.tw>; M.A. Monteiro <monteiro
uoguelph.ca>
Institutions: Department of Chemistry, University of Guelph, Guelph, ON, N1G 2W1, Canada, Department of Chemistry, University of Alberta, Edmonton, AB, T6G 2G2, Canada, Institute of Biological Chemistry, Academia Sinica, Nangang, Taipei, 11529, Taiwan, National Research Council Canada, Ottawa, ON, N1A 0R6, Canada, NMR Centre, University of Guelph, Guelph, ON, N1G 2W1, Canada, Department of Clinical Studies, University of Guelph, N1G 2W1, Guelph, ON, Canada, Department of Microbiology, University of Guelph, N1G 2W1, Guelph, ON, Canada, Institute of Biochemical Sciences, National Taiwan University, Taipei, 106, Taiwan
Enterocloster bolteae (formerly known as Clostridium bolteae) is a gastro-intestinal pathogenic bacterium often detected in the fecal microbiome of children in the autism spectrum. E. bolteae excretes metabolites that are thought to act as neurotoxins. This study is an update of our first E. bolteae investigation that discovered an immunogenic polysaccharide. Through a combination of chemical derivatizations/degradations, spectrometry and spectroscopy techniques, a polysaccharide composed of disaccharide repeating blocks comprised of 3-linked β-d-ribofuranose and 4-linked α-l-rhamnopyranose, [→3)-β-D-Ribf-(1→4)-α-L-Rhap-(1→]n, was identified. To confirm the structure, and to provide material for subsequent investigations, the chemical synthesis of a corresponding linker-equipped tetrasaccharide, β-D-Ribf-(1→4)-α-L-Rhap-(1→3)-β-D-Ribf-(1→4)-α-L-Rhap-(1→O(CH2)8N3, is also described. Research tools based on this immunogenic glycan structure can form the foundation for serotype classification, diagnostic/vaccine targets and clinical studies into the hypothesized role of E. bolteae in the onset/augmentation of autism related conditions in children.
polysaccharide, diarrhea, microbiome, Clostridium bolteae, autism, Enterocloster bolteae
Structure type: oligomer ; 750.3266 [M+Na]+
Location inside paper: table 1, abstract, p. 108805-9, Fig. 5, structure 3
Aglycon: (CH2)8N3, 8-azidooctyl
Trivial name: synthetic tetrasaccharide
Compound class: surface polysaccharide
Contained glycoepitopes: IEDB_136105,IEDB_149136,IEDB_225177,IEDB_885823
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, sugar analysis, TLC, chemical synthesis, HPLC, glycosylation, optical rotation measurement, HR-ESI-MS
Synthetic data: chemical
Related record ID(s): 22229
NCBI Taxonomy refs (TaxIDs): 208479
Show glycosyltransferases
NMR conditions: in D2O at 293 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,3,4 bDRibf 109.4 76.0 71.8 83.8 63.9
4,3 aLRhap 100.9-102.1 71.7-71.8 71.4-71.7 80.5-80.8 68.2 18.3
4 bDRibf 109.7 75.4 78.5 82.0 63.9
aLRhap 100.9-102.1 71.7-71.8 71.4-71.7 80.5-80.8 68.2 18.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,3,4 bDRibf 5.31 4.15 4.17 4.03 3.72-3.82
4,3 aLRhap 4.80-4.90 3.91-3.99 3.83-3.92 3.55 3.76-3.95 1.33-1.34
4 bDRibf 5.31 4.23 4.13 4.13 3.72
aLRhap 4.80-4.90 3.91-3.99 3.83-3.92 3.55 3.76-3.95 1.33-1.34
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,3,4 bDRibf 109.4/5.31 76.0/4.15 71.8/4.17 83.8/4.03 63.9/3.72-3.82
4,3 aLRhap 100.9-102.1/4.80-4.90 71.7-71.8/3.91-3.99 71.4-71.7/3.83-3.92 80.5-80.8/3.55 68.2/3.76-3.95 18.3/1.33-1.34
4 bDRibf 109.7/5.31 75.4/4.23 78.5/4.13 82.0/4.13 63.9/3.72
aLRhap 100.9-102.1/4.80-4.90 71.7-71.8/3.91-3.99 71.4-71.7/3.83-3.92 80.5-80.8/3.55 68.2/3.76-3.95 18.3/1.33-1.34
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,3,4 | bDRibf | 5.31 | 4.15 | 4.17 | 4.03 | 3.72
3.82 | |
| 4,3 | aLRhap | 4.80
4.90 | 3.91
3.99 | 3.83
3.92 | 3.55 | 3.76
3.95 | 1.33
1.34 |
| 4 | bDRibf | 5.31 | 4.23 | 4.13 | 4.13 | 3.72 | |
| | aLRhap | 4.80
4.90 | 3.91
3.99 | 3.83
3.92 | 3.55 | 3.76
3.95 | 1.33
1.34 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,3,4 | bDRibf | 109.4 | 76.0 | 71.8 | 83.8 | 63.9 | |
| 4,3 | aLRhap | 100.9
102.1 | 71.7
71.8 | 71.4
71.7 | 80.5
80.8 | 68.2 | 18.3 |
| 4 | bDRibf | 109.7 | 75.4 | 78.5 | 82.0 | 63.9 | |
| | aLRhap | 100.9
102.1 | 71.7
71.8 | 71.4
71.7 | 80.5
80.8 | 68.2 | 18.3 |
|
There is only one chemically distinct structure:
Found 
report error
(previously named: Clostridium bolteae 16351)