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01357 am a22001573u 4500 |
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342416 |
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|a Watts, Jonathan K.
|e author
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|a Jimenez-Barbero, Jesus
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|a Poveda, Ana
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|a Grindley, T. Bruce
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|a Control of disaccharide conformation through pi-stacking
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|c 2003-05.
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|z Get fulltext
|u https://eprints.soton.ac.uk/342416/1/2003_Watts_pi-stacking_-_CJC.pdf
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|a The conformations of a series of derivatives of the disaccharide α-L-fucopyranosyl-(1→3)-2-acetamido-2- deoxy-D-glucopyranoside, part of the Le<sup>x</sup> determinant, were studied by molecular modelling using the MM3* forcefield and by <sup>1</sup>H NMR spectroscopy. Unusually shielded O-benzyl protons were observed in the <sup>1</sup>H NMR spectrum of phenyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1→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.
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