Structural relationships in small molecule interactions governing gas-phase enantioselectivity and zwitterionic formation

Xin Cong, Gregg Czerwieniec, Erica McJimpsey, Seonghee Ahn, Frederic A. Troy, Carlito B Lebrilla

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Gas-phase zwitterionic amino acids were formed in complexes of underivatized β-cyclodextrin through reactions with a neutral base, n-propylamine. The reaction was performed in the analyzer cell of an electrospray ionization-Fourier transform mass spectrometer. Most of the natural amino acids were studied with three cyclodextrin hosts including α-, β-, and γ-cyclodextrin to understand better the structural features that lead to the stabilization of the zwitterionic complexes. Molecular dynamics calculations were performed to provide insight into the structural features of the complexes. The rate constants of the reactions were obtained through kinetic plots. Examination of both L- and D-enantiomers of the amino acid showed that the reaction was enantioselective. The reaction was then employed to analyze mixtures of Glu enantiomers naturally occurring in the bacteria Bacillus licheniformis.

Original languageEnglish (US)
Pages (from-to)442-452
Number of pages11
JournalJournal of the American Society for Mass Spectrometry
Volume17
Issue number3
DOIs
StatePublished - Mar 2006

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Enantioselectivity
Cyclodextrins
Enantiomers
Gases
Amino Acids
Molecules
Propylamines
Electrospray ionization
Mass spectrometers
Bacilli
Fourier Analysis
Molecular Dynamics Simulation
Molecular dynamics
Rate constants
Bacteria
Fourier transforms
Stabilization
Kinetics

ASJC Scopus subject areas

  • Structural Biology
  • Spectroscopy

Cite this

Structural relationships in small molecule interactions governing gas-phase enantioselectivity and zwitterionic formation. / Cong, Xin; Czerwieniec, Gregg; McJimpsey, Erica; Ahn, Seonghee; Troy, Frederic A.; Lebrilla, Carlito B.

In: Journal of the American Society for Mass Spectrometry, Vol. 17, No. 3, 03.2006, p. 442-452.

Research output: Contribution to journalArticle

Cong, Xin ; Czerwieniec, Gregg ; McJimpsey, Erica ; Ahn, Seonghee ; Troy, Frederic A. ; Lebrilla, Carlito B. / Structural relationships in small molecule interactions governing gas-phase enantioselectivity and zwitterionic formation. In: Journal of the American Society for Mass Spectrometry. 2006 ; Vol. 17, No. 3. pp. 442-452.
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