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Transition states for glucopyranose interconversion.

Brett E Lewis1, Nankishoresing Choytun, Vern L Schramm

  • 1Department of Biochemistry, Albert Einstein College of Medicine, 1300 Morris Park Avenue, Bronx, New York 10461, USA.

Journal of the American Chemical Society
|April 13, 2006
PubMed
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Researchers elucidated the transition states of glucose anomerization using kinetic isotope effects and computational modeling. This study reveals key molecular structures and interactions governing this fundamental biological and chemical reaction.

Area of Science:

  • Carbohydrate Chemistry
  • Biophysical Chemistry
  • Computational Chemistry

Background:

  • Glucose anomerization is a fundamental reaction in biology and chemistry, crucial for understanding carbohydrate behavior.
  • The precise transition-state structures governing glucose anomerization have remained elusive, hindering a complete understanding of its solution chemistry.
  • Elucidating these structures is key to advancing knowledge in glycobiology and chemical kinetics.

Purpose of the Study:

  • To determine the transition-state structures for the anomerization of glucose.
  • To investigate the role of water in the transition states of glucose anomerization.
  • To provide high-level computational models constrained by experimental kinetic data.

Main Methods:

  • Kinetic isotope effects (KIEs) were measured for the interconversion of alpha- and beta-glucopyranose.

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  • Saturation transfer 13C Nuclear Magnetic Resonance (NMR) spectroscopy was used to determine relative free energies of transition states.
  • High-level computational theory was employed to model transition states, incorporating primary, secondary, and solvent KIEs.

    • Main Results:

    • Experimental KIEs were converted to unidirectional KIEs using equilibrium isotope effects.
    • Relative free energies of the ring-opening and ring-closing transition states were determined via NMR spectroscopy.
    • Computational models successfully identified the transition states for anomerization, consistent with experimental KIEs.

    Conclusions:

    • The study successfully identified the transition states for glucose anomerization.
    • It was determined that water cannot simultaneously form a hydrogen bond bridge to both the OH1 and O5 hydroxyl groups of glucose in either transition state.
    • These findings provide critical insights into the mechanism of glucose anomerization and the role of solvation.