Kaji E, Anabuki N, Zen S Syntheses of three interglycosidic isomers of N-acetyl-b-D-mannosaminyl-L-rhamnoses associated with O-antigens of several gram-negative opportunistic pathogens Chemical and Pharmaceutical Bulletin43 (1995)
1441-1447
NCBI PubMed ID:7586068 Journal NLM ID:0377775 Publisher: 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.
Synthetic data: chemical Comments, role: the disaccharide associated with O-antigen of Escherichia coli O1A
Related record ID(s): 7178, 7220, 7221, 7222, 7224 NCBI Taxonomy refs (TaxIDs):562 Reference(s) to other database(s): GTC:G47266GW, GlycomeDB:27120 Show glycosyltransferases
There are 3 chemically distinct structures. Please, select:
Found 
report error
