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Mechanism of Glucose Isomerization Using a Solid Lewis Acid Catalyst in Water

Authors

  • Dr. Yuriy Román-Leshkov,

    1. Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA), Fax: (+1) 626-568-8743
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    • These authors contributed equally to this work.

  • Dr. Manuel Moliner,

    1. Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA), Fax: (+1) 626-568-8743
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    • These authors contributed equally to this work.

  • Dr. Jay A. Labinger,

    1. Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA), Fax: (+1) 626-568-8743
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  • Prof. Mark E. Davis

    Corresponding author
    1. Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA), Fax: (+1) 626-568-8743
    • Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA), Fax: (+1) 626-568-8743
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  • This work was financially supported as part of the Catalysis Center for Energy Innovation, an Energy Frontier Research Center funded by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under Award Number DE-SC00010004. M.M. acknowledges Fundación Ramón Areces Postdoctoral Research Fellowship Program for financial support.

Abstract

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Other way round: 1H and 13C NMR spectroscopy on isotopically labeled glucose reveals that in the presence of tin-containing zeolite Sn-Beta, the isomerization reaction of glucose in water proceeds by way of an intramolecular hydride shift (see scheme) rather than proton transfer. This is the first mechanistic demonstration of Sn-Beta acting as a Lewis acid in a purely aqueous environment.

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