Synthesis of the unique trisaccharide repeating unit, isolated from lipopolysaccharides Rhizobium leguminosarum bv. trifolii 24, and its analogue.
The synthesis of trisaccharide: 6-d-alpha-L-Talp(1-->2)-alpha-L-Rhap(1-->5)-DHA, and its analogue: 6-d-alpha-L-Talp(1-->2)-beta-L-Rhaf(1-->5)DHA is described. In the first step a disaccharide, composed of 6-d-L-Talp and L-Rhap was obtained. This, in turn, was converted to the corresponding 1-trichloroacetimidate and coupled with DHA alcohol to afford the required trisaccharide. Its analogue was achieved by the conversion of the above disaccharide to the glycosyl bromide, involving the rhamnopyranose ring scission, followed by condensation with DHA in Koenigs-Knorr procedure.
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Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland.
D002240:Carbohydrate Sequence; D008070:Lipopolysaccharides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D011135:Polysaccharides, Bacterial / Q000737:chemistry*; D016961:Rhizobium leguminosarum / Q000737:chemistry*; D014312:Trisaccharides / Q000138:chemical synthesis*
D008070:Lipopolysaccharides; D011135:Polysaccharides, Bacterial; D014312:Trisaccharides; C113369:talopyranosyl-(1-2)-rhamnopyranosyl-(1-5)-3-deoxyheptulosaric acid