Abstract

We have used the hydroxyl protons of sucrose dissolved in supercooled water as NMR probes for the detection of intramolecular hydrogen bonds. Neither the measured OH temperature shift coefficients, 3 J HCOH scalar couplings, isotope-induced 13C chemical shifts (Δδ COH/COD) nor OH exchange rates allowed us to single out any hydroxyl group in sucrose with characteristics indicative of involvement in strong hydrogen bonding. However, two-dimensional rotating-frame exchange (ROESY) spectroscopy revealed a direct exchange between the glucosyl OH2 and fructosyl OH1 protons. We conclude that an O2g::H::O1f interresidue hydrogen bond transiently exists in sucrose in aqueous solution. ROESY of sugars in supercooled water is proposed as a novel method to detect this type of weak hydrogen bonding.

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