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Control of disaccharide conformation through pi-stacking

Control of disaccharide conformation through pi-stacking
Control of disaccharide conformation through pi-stacking
The conformations of a series of derivatives of the disaccharide α-L-fucopyranosyl-(1→3)-2-acetamido-2- deoxy-D-glucopyranoside, part of the Lex determinant, were studied by molecular modelling using the MM3* forcefield and by 1H NMR spectroscopy. Unusually shielded O-benzyl protons were observed in the 1H 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.
364-375
Watts, Jonathan K.
c4de85ee-aaa3-4e7d-99b3-147a4de4f01c
Jimenez-Barbero, Jesus
84e4df1a-b6e9-4d7d-98b4-817fb9dc5e49
Poveda, Ana
3e273b6d-620f-4678-becd-3af0bb7fe34a
Grindley, T. Bruce
f413d8cb-993a-4146-bf9e-8c9d07f412a9
Watts, Jonathan K.
c4de85ee-aaa3-4e7d-99b3-147a4de4f01c
Jimenez-Barbero, Jesus
84e4df1a-b6e9-4d7d-98b4-817fb9dc5e49
Poveda, Ana
3e273b6d-620f-4678-becd-3af0bb7fe34a
Grindley, T. Bruce
f413d8cb-993a-4146-bf9e-8c9d07f412a9

Watts, Jonathan K., Jimenez-Barbero, Jesus, Poveda, Ana and Grindley, T. Bruce (2003) Control of disaccharide conformation through pi-stacking. Canadian Journal of Chemistry, 81 (5), 364-375. (doi:10.1139/V03-062).

Record type: Article

Abstract

The conformations of a series of derivatives of the disaccharide α-L-fucopyranosyl-(1→3)-2-acetamido-2- deoxy-D-glucopyranoside, part of the Lex determinant, were studied by molecular modelling using the MM3* forcefield and by 1H NMR spectroscopy. Unusually shielded O-benzyl protons were observed in the 1H 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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Published date: May 2003
Organisations: Organic Chemistry: SCF

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Local EPrints ID: 342416
URI: http://eprints.soton.ac.uk/id/eprint/342416
PURE UUID: 8429e2fe-4283-4423-8dac-b1f0288347a8

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Date deposited: 12 Sep 2012 11:31
Last modified: 19 Jul 2019 21:54

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