Conformational effects in sugar ions: Spectroscopic investigations in the gas phase and in solution

Ram Sagar, Svemir Rudić, David P. Gamblin, Eoin M. Scanlan, Timothy D. Vaden, Barbara Odell, Timothy D.W. Claridge, John P. Simons, Benjamin G. Davis

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)2307-2313
Number of pages7
JournalChemical Science
Volume3
Issue number7
DOIs
StatePublished - Jul 2012

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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