Chiral recognition in gas-phase cyclodextrin: amino acid complexes - Is the three point interaction still valid in the gas phase?

Seonghee Ahn, Javier Ramirez, Gabriela Grigorean, Carlito B Lebrilla

Research output: Contribution to journalArticle

87 Citations (Scopus)

Abstract

The validity of the 'three-point interaction' model is examined in the guest exchange reaction involving complexes of cyclodextrins and amino acids. The amino acid guest is exchanged in the gas phase in the presence of a gaseous alkyl amine. The net reaction is proton transfer between the protonated amino acid and the alkyl amine. The amino acid is lost as a neutral species. This reaction is sensitive to the chirality of the amino acid. Several amino acids are examined as well as the respective methyl esters to determine the role of the three interacting groups (ammonium, carboxylic acid, and side chain) in enantioselectivity. We find that the three-point interaction model is indeed valid in the gas phase. Enantioselectivity is optimal when two points of attraction and one repulsion is present in the gas-phase complex. The results are supported by molecular modeling calculations. A mechanism for the exchange is proposed.

Original languageEnglish (US)
Pages (from-to)278-287
Number of pages10
JournalJournal of the American Society for Mass Spectrometry
Volume12
Issue number3
DOIs
StatePublished - 2001

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Cyclodextrins
Gases
Amino Acids
Enantioselectivity
Amines
Proton transfer
Molecular modeling
Chirality
Carboxylic Acids
Ammonium Compounds
Protons
Esters

ASJC Scopus subject areas

  • Structural Biology
  • Spectroscopy

Cite this

Chiral recognition in gas-phase cyclodextrin : amino acid complexes - Is the three point interaction still valid in the gas phase? / Ahn, Seonghee; Ramirez, Javier; Grigorean, Gabriela; Lebrilla, Carlito B.

In: Journal of the American Society for Mass Spectrometry, Vol. 12, No. 3, 2001, p. 278-287.

Research output: Contribution to journalArticle

Ahn, Seonghee ; Ramirez, Javier ; Grigorean, Gabriela ; Lebrilla, Carlito B. / Chiral recognition in gas-phase cyclodextrin : amino acid complexes - Is the three point interaction still valid in the gas phase?. In: Journal of the American Society for Mass Spectrometry. 2001 ; Vol. 12, No. 3. pp. 278-287.
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