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Modeling ring puckering in strained systems: application to 3,6-anhydroglycosides.

Diego A Navarro1, Carlos A Stortz

  • 1Departamento de Química Orgánica-CIHIDECAR, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina.

Carbohydrate Research
|July 19, 2005
PubMed
Summary

Methyl 3,6-anhydroglycosides adopt distorted chair conformations, with boat forms being more stable than previously thought. Computational methods reveal nuances in conformational preferences influenced by configuration and anomeric effects.

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Area of Science:

  • Carbohydrate Chemistry
  • Computational Chemistry
  • Structural Chemistry

Background:

  • Methyl 3,6-anhydroglycosides are important structural motifs in carbohydrates.
  • Understanding their conformational preferences is crucial for predicting their behavior and properties.

Purpose of the Study:

  • To investigate the conformational landscape of methyl 3,6-anhydroglycosides with beta-D-galacto, alpha-D-galacto, and beta-D-gluco configurations.
  • To compare the accuracy of molecular mechanics (MM3) and quantum mechanical (QM) methods in predicting these conformations.

Main Methods:

  • Molecular mechanics (MM3) simulations were performed, plotting energies against Cremer and Pople puckering coordinates.
  • Quantum mechanical (QM) calculations were conducted at HF/- and B3LYP/6-31+G** levels, with and without solvent emulation.

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  • Experimental data in solution were used for comparison.

    • Main Results:

    • Both MM3 and QM methods identified distorted chair ((1)C(4)) and boat (B(1,4)) conformations as the most likely for the six-membered ring.
    • MM3 and HF calculations suggested a preference for the chair conformation, but DFT calculations indicated smaller energy differences, implying underestimated stability of boat conformations.
    • Experimental data confirmed the prevalence of chair conformations for most derivatives, with some showing a mix of chair and boat forms depending on the solvent.

    Conclusions:

    • Computational methods provide valuable insights into the conformational preferences of methyl 3,6-anhydroglycosides.
    • DFT calculations offer a more accurate representation of conformational energies compared to MM3 and HF methods.
    • The anomeric effect plays a significant role in dictating conformational preferences in these strained glycosidic systems.