TUD Organische ChemieImmelStructuresCHIME - Fructose (Informations)View or Print this frame onlyView or Print (this frame only)

Fructose - Five Different Tautomers

Molecular Modeling of Saccharides, Part III. Sucrose, Sucralose, and Fructose: Correlations Between Hydrophobicity Potential Profiles and AH-B-X Assignments.
F. W. Lichtenthaler and S. Immel, in: Sweet Taste Chemoreception (Eds.: M. Mathlouthi, J. A. Kanters, and G. G. Birch), Elsevier Appl. Science, London/New York, 1993, pp. 21-53.

D-Fructose in aqueous solution is a complicated equilibrium of five different tautomeric forms (i.e. α- and β-fructopyranose, α- and β-fructofuranose, and keto-fructose), all of which can rapidly interconvert into each other. The major form is the β-pyranoid tautomer, followed by the β-furanoid isomer; the other compounds play only a minor role in the solution equilibrium. All structures displayed here are global energy-minimum conformations as obtained with the PIMM force-field[1].

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  1. (a) H. J. Lindner, PIMM88 - Closed Shell PI-SCF-LCAO-MO- Molecular Mechanics Program, Technical University of Darmstadt, 1988. - (b) H. J. Lindner, Tetrahedron 1974, 30, 1127-1132. - (c) A. E. Smith, Ph.D. Thesis, Technical University of Darmstadt, 1989. - (d) A. E. Smith and H. J. Lindner, J. Comput.-Aided Mol. Des. 1991, 5, 235-262.

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