Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: infection due to Bacillus anthracis [ICD11:
XN94F 
]
The structure was elucidated in this paperNCBI PubMed ID: 16216230Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: kpn
helix.nih.gov
Institutions: NIDDK, LMC, National Institutes of Health, Bethesda, MD 20892-0815, USA
The beta glycoside of the tetrasaccharide sequence β-Ant-(1→3)-α-L-Rhap-(1→3)-α-L-Rhap-(1→2)-l-Rhap, whose aglycon allows conjugation to proteins, was synthesized for the first time. A stepwise synthetic approach was applied with thioglycosides as glycosyl donors, and the beta anomer of the compound was obtained equipped with a spacer group whose further transformation allows conjugation to suitable carriers. To synthesize the β-anthrosyl linkage with high stereoselectivity, a linker-equipped rhamnotriose derivative was glycosylated with ethyl 4-azido-3-O-benzyl-2-O-bromoacetyl-4,6-dideoxy-1-thio-β-D-glucopyranosi de. Further functionalization of the tetrasaccharide thus obtained, followed by deprotection, gave the target substance.
oligosaccharide, Anthrax, Anthrose, Exosporium glycoprotein, Thioglycoside
Structure type: oligomer
Location inside paper: scheme 3, compound 17
Aglycon: 5-methoxycarbonylpentyl
Trivial name: anthrose tetrasaccharide
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_225177,IEDB_885823
Methods: NMR, TLC, chemical synthesis, chemical methods
Synthetic data: chemical
Comments, role: tetrasaccharide chain of the major glycoprotein of exosporium
NCBI Taxonomy refs (TaxIDs): 1392Reference(s) to other database(s): GlycomeDB:
27761
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
report error