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Related Experiment Videos

Zwitterion formation in gas-phase cyclodextrin complexes.

Seonghee Ahn1, Xin Cong, Carlito B Lebrilla

  • 1Department of Chemistry, School of Medicine, University of California at Davis, Davis, California 95616, USA.

Journal of the American Society for Mass Spectrometry
|February 8, 2005
PubMed
Summary

Amino acids and beta-cyclodextrin form ternary complexes with alkyl amines. These complexes are salt-bridge zwitterionic species, stabilized by interactions with cyclodextrin hydroxyl groups.

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Area of Science:

  • Analytical Chemistry
  • Supramolecular Chemistry
  • Mass Spectrometry

Background:

  • Beta-cyclodextrins (CDs) are cyclic oligosaccharides with a hydrophobic cavity and hydrophilic exterior.
  • Amino acids are the building blocks of proteins and play crucial roles in biological systems.
  • Electrospray ionization (ESI) is a soft ionization technique widely used in mass spectrometry.

Purpose of the Study:

  • To investigate the formation and structure of ternary complexes involving protonated amino acids, beta-cyclodextrin, and alkyl amines.
  • To elucidate the non-covalent interactions stabilizing these ternary complexes.

Main Methods:

  • Electrospray ionization mass spectrometry (ESI-MS) was used to generate and analyze protonated complexes.
  • Complexes were trapped in a Fourier transform mass spectrometer (FT-MS) for further reaction and analysis.

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  • Molecular modeling calculations were employed to complement experimental findings.

    • Main Results:

    • Protonated complexes of amino acids and beta-cyclodextrin reacted with alkyl amines to form ternary complexes.
    • The ternary complexes were identified as salt-bridge zwitterionic species.
    • These species involve amino acid zwitterions and protonated alkylamines interacting with the hydroxyl groups on the narrow rim of beta-cyclodextrin.

    Conclusions:

    • The formation of ternary complexes is driven by the zwitterionic nature of amino acids and the protonated alkylamines.
    • Interactions between the amino acid residues and the hydroxyl groups on the cyclodextrin rim are critical for complex stabilization.
    • This study provides insights into the non-covalent interactions governing the assembly of supramolecular structures.