Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
NCBI PubMed ID: 7586068Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, Kiiasaw University, Shirokane 5-9-1, Minato-ku, Tokyo IDS, Japan, School of Pharmaceutical Sciences, Kiiasaw University, Shirokane 5-9-1, Minato-ku, Tokyo IDS, Japan.
We achieved practical, highly stereoselective syntheses of three interglycosidic isomers of N-acetyl-β-D-mannosaminyl-L-rhamnoses, among which a β(1→4)-isomer corresponds to the repeating unit of the O-antigen of lipopolysaccharide (LPS) from the opportunistic pathogens Pseudomonas cepacia O5 and Pseudomonas aeruginosa X (Meitert). The other isomers are a β(1→2)-disaccharide, a constituent of LPS from Escherichia coli O1A, and an artificial β(1→3)-isomer. The disaccharides were obtained by simple three-step reaction sequences from 2-(benzoyloxyimino)-2-deoxyglycosyl halides (mannosamine progenitor). β-Selective glycosylations of appropriately protected L-rhamnosyl acceptors were performed. Subsequent reduction of the 2-acyloxyimino function to an amino group, N-acetylation, and removal of the protecting groups provided the target disaccharides. 13C NMR and nuclear Overhauser effect spectra proved to be useful for structural determination of the positional isomers of the disaccharides.
Lipopolysaccharide, O-antigen, Gram-negative bacteria, 2-amino-2-deoxy-D-mannose, β-3-D-mannosaminyl-L-rhamnose, 2-uiose oxime, opportunistic infection
Structure type: polymer chemical repeating unit
Location inside paper: p.1441, fig.1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135610,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_225177,IEDB_885813,IEDB_885823
Synthetic data: chemical
Related record ID(s): 7178, 7220, 7221, 7223, 7224, 20630, 116148
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G57484QO, GlycomeDB:
6035
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
report error