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Structural characteristics of cyclodextrins in the solid state.

K B Lipkowitz1, K Green, J A Yang

  • 1Department of Chemistry, Indiana University-Purdue University at Indianapolis 46205.

Chirality
|January 1, 1992
PubMed
Summary
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Solid-state cyclodextrins (alpha-, beta-, and gamma-) adopt high-energy shapes. Molecular mechanics reveal these structures differ significantly from their most stable, low-energy conformations.

Area of Science:

  • Supramolecular Chemistry
  • Solid-State Chemistry
  • Computational Chemistry

Background:

  • Cyclodextrins are cyclic oligosaccharides with unique inclusion properties.
  • Understanding their solid-state conformations is crucial for applications.
  • Previous studies often focused on solution-state behavior.

Purpose of the Study:

  • To compare solid-state structures of alpha-, beta-, and gamma-cyclodextrins.
  • To analyze monomeric and macromolecular features influencing cyclodextrin shape.
  • To investigate the impact of guest inclusion on solid-state conformations.

Main Methods:

  • Analysis of monomeric features: primary hydroxyl group orientation and pyranose ring pucker.
  • Examination of macromolecular features: oligomer planarity, pyranose ring tilting, and symmetry deviation.

Related Experiment Videos

  • Application of molecular mechanics calculations using MM2, AMBER, and CHARMM force fields.

    • Main Results:

    • Solid-state cyclodextrins exhibit significant deviations from ideal symmetry.
    • Both guest-free and guest-bound cyclodextrins were analyzed for shape descriptors.
    • Calculations indicate most solid-state forms are high-energy conformations.

    Conclusions:

    • Solid-state cyclodextrins are conformationally constrained in high-energy states.
    • These trapped conformations differ substantially from the most stable calculated forms.
    • Force field calculations provide insights into the energetic landscape of cyclodextrin structures.