Zwitterion formation in gas-phase cyclodextrin complexes

Seonghee Ahn, Xin Cong, Carlito B Lebrilla, Scott Gronert

Research output: Contribution to journalArticle

24 Scopus citations

Abstract

Protonated complexes of amino acids and underivatized β-cyclodextrin, produced by electrospray ionization and trapped in the Fourier transform mass spectrometer, undergo formation of ternary complexes when reacted with alkyl amine. Based on the reactivities of the protonated amino acid complexes with alkylamines, the reactivities of the corresponding amino acid esters, and partially derivatized β-cyclodextrin hosts, we conclude that the ternary complexes are salt-bridge zwitterionic species composed of amino acid zwitterions and protonated alkylamine all interacting with the hydroxyl groups on the narrow rim of the cyclodextrin. Molecular modeling calculations and experimental results suggest that the interactions of the amino acids with the rims contribute greatly to the formation of the zwitterionic species.

Original languageEnglish (US)
Pages (from-to)166-175
Number of pages10
JournalJournal of the American Society for Mass Spectrometry
Volume16
Issue number2
DOIs
StatePublished - Feb 2005

ASJC Scopus subject areas

  • Structural Biology
  • Spectroscopy

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