Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: periodontitis [ICD11:
DA0C 
]
The structure was elucidated in this paperPublication DOI: 10.1039/d0qo00704hJournal NLM ID: 101630631Publisher: London: RSC Publishing
Correspondence: yjs
scu.edu.cn
Institutions: Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, Department of Chemistry of Medicinal Natural Products, West China School of Pharmacy, Sichuan University, Chengdu 610041, China
Eubacterium saburreum is one of the human oral pathogens and has been proved to play a significant role in the development of periodontal diseases. The cell-surface polysaccharides expressed by this microorganism are attractive targets for the development of carbohydrate-based diagnostic tools or therapeutics against oral bacteria. Here, we report the first chemical synthesis of a structurally unusual hexasaccharide repeat 1 found in the cell wall polysaccharide of E. saburreumstrain T19. This linear oligosaccharide is composed of two parts: one is an α-(1→2)-linked d-fucofuranosyl disaccharide, and the other is an alternating β-(1→3)- and (1→6)-linked d-glycero-d-galacto-heptopyranosyl tetrasaccharide. The two fragments are connected via an α-d-fucofuranosidic linkage. A number of synthetic challenges had to be addressed, including the development of new chemistry for efficient formation of d-galactoheptopyranoside, the development of stereoselective glycosylation methods for the construction of 1,2-cis-α-d-fucofuranosidic bonds, and the screening of appropriate conditions for the assembly of the sterically congested trisaccharide portion at the non-reducing end of the target molecule. Through a convergent [3 + 3] coupling strategy, the left trisaccharide thioglycoside donor 17d and the right trisaccharide 3,4-diol acceptor 26 were efficiently forged together to generate the whole molecular backbone, thus leading to the total synthesis of 1. (formula: see text)
heptose, hexasaccharide, repeating unit, glycosylation, antigenic polysaccharide, Eubacterium saburreum, total synthesis, stereoselective synthesis, Periodontal disease
Structure type: oligomer
Location inside paper: p.2299, Scheme 1, p.2303, Scheme 5, compound 1
Aglycon: (->1)3-aminopropyl
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_142489,SB_86
Methods: 13C NMR, 1H NMR, ESI-MS, chemical synthesis, glycosylation
Synthetic data: chemical
Related record ID(s): 32174
NCBI Taxonomy refs (TaxIDs): 467210Reference(s) to other database(s): GTC:G83502GY
Show glycosyltransferases
There is only one chemically distinct structure:
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(later renamed to: Lachnoanaerobaculum saburreum T19)