Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: diarrhea [ICD11:
ME05.1 
, ICD11:
SA55 ];
autism spectrum disorder (ASD) [ICD11:
6A02 ]
NCBI PubMed ID: 35333269Publication DOI: 10.1039/d2ob00131dJournal NLM ID: 101154995Publisher: The Royal Society of Chemistry
Correspondence: fauzanne
uoguelph.ca
Institutions: Department of Chemistry, University of Guelph, Guelph, Ontario N1G 2W1, Canada, Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada
Many children suffering from autism spectrum disorder (ASD) experience gastrointestinal (GI) conditions. Enterocloster bolteae has been regularly detected in the stool of individuals suffering from GI symptoms and autism. Literature has suggested that E. bolteae strains WAL 16351 and WAL 14578 produce an immunogenic capsular polysaccharide (CPS) comprised of disaccharide repeating units: α-D-Man-(1→4)-β-Rha-(1→3) that could be used for the development of an immunotherapeutic vaccine. Ambiguity in the configuration of rhamnose led to the synthesis of tri- and disaccharide analogues containing D-rhamnose and L-rhamnose, respectively. ROESY-NMR spectra showed that CH3-6 of rhamnose and H-2 of mannose in the L-Rha containing disaccharide gave correlation. No such correlation was seen between the CH3-6 of rhamnose and the H-2 of mannose in the D-Rha containing trisaccharide. Molecular dynamics studies on hexasaccharide containing L-Rha or D-Rha confirmed that these structures adopt conformations resulting in different distances between the C6-rhamnose and the H-2 mannose of the preceding residue. We also demonstrate that assignment of the absolute configuration of the rhamnosyl residue in the β-Rhap-(1→3)-D-Man linkage can be determined using the 13C chemical shift of C-2 in of D-Mannose. While β-D-Rha will lead to an upfield shift of C-2 due to γ-gauche interaction between H-1 Rha and H-2 Man, β-L-Rha will not. Our results provide insights to distinguish between D- and L-rhamnose in the α-D-Manp-(1→4)-β-Rhap-(1→3) repeating motif.
NMR, conformation, synthesis, structure, D-mannose, capsular polysaccharide, molecular dynamics, L-rhamnose, vaccine, D-rhamnose
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p. 2965, table 4
Compound class: CPS
Contained glycoepitopes: IEDB_130701,IEDB_1394181,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, chemical synthesis, MD simulations, HPLC, glycosylation, 1D ROESY
3D data: molecular modeling
Related record ID(s): 20867, 20868
NCBI Taxonomy refs (TaxIDs): 208479Reference(s) to other database(s): GTC:G64150GO
Show glycosyltransferases
There is only one chemically distinct structure:
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(previously named: Clostridium bolteae WAL 16351)