Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Salmonella enterica [ICD11:
XN5VC 
];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperPublication DOI: 10.1002/1099-0690(200109)Journal NLM ID: 9805750Publisher: Wiley-VCH
Correspondence: G. Widmalm <gw
organ.su.se>
Institutions: Departement of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
The synthesis of three trisaccharides related to the branching region in the O-antigen polysaccharides from E. coli O35 and S. arizona O62 is reported. A regioselective b-glycosylation was performed at O-3 of a methyl a-L-rhamnopyranoside derivative. cis-Glycosylation of an a-D-galactosamine derivative at O-2 of the methyl a-L-rhamnopyranoside took place in excellent yield (90%) to produce, after deprotection, compound 1. Functionalization at C-6 of the a-D-galactosamine residue by regioselective TEMPO oxidation resulted in the corresponding uronic acid, which subsequently gave 2. Treatment of an activated ester, derived from the uronic acid, with ammonia provided the desired carboxamide, and subsequently 3.
glycosylation, natural products, oligosacchride, oxidation
Structure type: oligomer
Location inside paper: Fig. 1
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_225177,IEDB_885822,IEDB_885823
Synthetic data: chemical
Comments, role: synthetic oligosaccharide similar to OPS fragment of Escherichia coli O35 and Salmonella arizonae O62
Related record ID(s): 9011
NCBI Taxonomy refs (TaxIDs): 59203,
2072460Reference(s) to other database(s): GlycomeDB:
27341
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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(later renamed to: Salmonella enterica ssp. arizonae O62)