Observation of the keto tautomer of D-fructose in D2O using 1H NMR spectroscopy

Thomas Barclay, Milena Ginic-Markovic, Martin Johnston, Peter Cooper, Nikolai Petrovsky

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    78 Citations (Scopus)

    Abstract

    d-Fructose was analysed by NMR spectroscopy and previously unidentified 1H NMR resonances were assigned to the keto and α-pyranose tautomers. The full assignment of shifts for the various fructose tautomers enabled the use of 1H NMR spectroscopy in studies of the mutarotation (5-25 °C) and tautomeric composition at equilibrium (5-50 °C). The mutarotation of β-pyranose to furanose tautomers in D 2O at a concentration of 0.18 M was found to have an activation energy of 62.6 kJ mol -1. At tautomeric equilibrium (20 °C in D 2O) the distribution of the β-pyranose, β-furanose, α-furanose, α-pyranose and the keto tautomers was found to be 68.23%, 22.35%, 6.24%, 2.67% and 0.50%, respectively. This tautomeric composition was not significantly affected by varying concentrations between 0.089 and 0.36 M or acidification to pH 3. Upon equilibrating at 6 temperatures between 5 and 50 °C there was a linear relationship between the change in concentration and temperature for all forms.

    Original languageEnglish
    Pages (from-to)136-141
    Number of pages6
    JournalCarbohydrate Research
    Volume347
    Issue number1
    DOIs
    Publication statusPublished - 2012

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