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: 32734715Publication DOI: 10.1002/anie.202007209Journal NLM ID: 0370543Publisher: Weinheim: Wiley-VCH
Correspondence: jianyin
jiangnan.edu.cn
Institutions: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Potsdam, Germany, Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Lihu Avenue 1800, Wuxi, Jiangsu Province, 214122 P. R. China
The gut pathogen Clostridium bolteae has been associated with the onset of autism spectrum disorder (ASD). To create vaccines against C. bolteae, it is important to identify exact protective epitopes of the immunologically active capsular polysaccharide (CPS). Here, a series of C. bolteae CPS glycans, up to an octadecasaccharide, was prepared. Key to achieving the total syntheses is a [2+2] coupling strategy based on a β-d-Rhap-(1→3)-α-d-Manp repeating unit that in turn was accessed by a stereoselective β-d-rhamnosylation. The 4,6-O-benzylidene-induced conformational locking is a powerful strategy for forming a β-d-mannose-type glycoside. An indirect strategy based on C2 epimerization of β-d-quinovoside was efficiently achieved by Swern oxidation and borohydride reduction. Sequential glycosylation, and regioselective and global deprotection produced the disaccharide and tetrasaccharide, up to the octadecasaccharide. Glycan microarray analysis of sera from rabbits immunized with inactivated C. bolteae bacteria revealed a humoral immune response to the di- and tetrasaccharide, but none of the longer sequences. The tetrasaccharide may be a key motif for designing glycoconjugate vaccines against C. bolteae.
carbohydrate, immunology, polysaccharides, Clostridium, glycoconjugate, total synthesis, carbohydrate chemistry
Structure type: oligomer
Location inside paper: p.20715, scheme 5, octadecasaccharide 1
Aglycon: (1->1)(CH2)5NH2 (5-aminopentyl)
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, IR, TLC, chemical synthesis, chemical methods, glycosylation, conjugation, HR-ESI-MS
Synthetic data: chemical
Related record ID(s): 32070
NCBI Taxonomy refs (TaxIDs): 208479Reference(s) to other database(s): GTC:G90155XL
Show glycosyltransferases
There is only one chemically distinct structure:
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(later renamed to: Enterocloster bolteae)