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Issue 7, 2012
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Conformational effects in sugar ions: spectroscopic investigations in the gas phase and in solution

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Abstract

We present direct investigations of the conformational preferences of sugars with a positively charged substituent at their anomeric centre, C-1, which display in solution, a preference for an equatorial conformation—an apparent reversal of the normal anomeric effect. The investigations focus on the protonated monosaccharide, D-xylopyranosyl imidazolium in its α and β forms, first probed in a range of different solvents through NMR measurements and then in the gas phase, free of solvent or counterion interactions, through infrared multiphoton dissociation spectroscopy. The results, when compared and discussed in the light of density functional theory, ab initio and natural bond orbital calculations, expose the possible origins of the reversed conformational preference and provide a better understanding of the factors controlling conformational choice.

Graphical abstract: Conformational effects in sugar ions: spectroscopic investigations in the gas phase and in solution

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Publication details

The article was received on 18 Mar 2012, accepted on 25 Apr 2012 and first published on 25 Apr 2012


Article type: Edge Article
DOI: 10.1039/C2SC20341C
Citation: Chem. Sci., 2012,3, 2307-2313
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    Conformational effects in sugar ions: spectroscopic investigations in the gas phase and in solution

    R. Sagar, S. Rudić, D. P. Gamblin, E. M. Scanlan, T. D. Vaden, B. Odell, T. D. W. Claridge, J. P. Simons and B. G. Davis, Chem. Sci., 2012, 3, 2307
    DOI: 10.1039/C2SC20341C

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