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- W2103993604 abstract "The conformations of a series of derivatives of the disaccharide α-L-fucopyranosyl-(1[Formula: see text]3)-2-acetamido-2-deoxy-D-glucopyranoside, part of the Le x determinant, were studied by molecular modelling using the MM3* forcefield and by 1 H NMR spectroscopy. Unusually shielded O-benzyl protons were observed in the 1 H NMR spectrum of phenyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1[Formula: see text]3)-2-deoxy-2-phthalimido-1-thio-α-D-glucopyranoside and assigned to the 2-O-benzyl group. This observation was explained by a shift in the population of the conformational mixture present about the glycosidic linkage from the positive Ψ region in the unsubstituted disaccharide to the negative Ψ region induced by π-stacking between the phthalimide and the 2-O-benzyl phenyl ring. The experimental nuclear Overhauser enhancements confirm the accuracy of the calculations.Key words: disaccharide, conformation, π-stacking, Le x determinant, NOE measurements, MM3 calculations." @default.
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- W2103993604 date "2003-05-01" @default.
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- W2103993604 title "Control of disaccharide conformation by π-stacking" @default.
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- W2103993604 doi "https://doi.org/10.1139/v03-062" @default.
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