Chiral Differentiation of Some Cyclopentane and Cyclohexane β-Amino Acid Enantiomers Through Ion/Molecule Reactions

Anna R.M. Hyyryläinen, Jaana M.H. Pakarinen, Eniko Forró, Ferenc Fülöp, Pirjo Vainiotalo

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18 Citations (Scopus)

Abstract

Chiral differentiation of four enantiomeric pairs of β-amino acids, cis-(1R,2S)-, cis-(1S,2R)-, trans-(1R,2R)-, and trans-(1S,2S)-2-aminocyclopentanecarboxylic acids (cyclopentane β-amino acids), and cis-(1R,2S)-, cis-(1S,2R)-, trans-(1R,2R)-, and trans-(1S,2S)-2-aminocyclohexanecarboxylic acids (cyclohexane β-amino acids) was performed successfully by using host-guest complexes and ion/molecule reactions. The experiments were conducted by using electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry. The effect of a chiral host molecule was tested by using three different host compounds; (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid, (-)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid, and β-cyclodextrin. This is the first time that small enantiomeric pairs with two chiral centers have been differentiated using ion/molecule reactions and host-guest complexes.

Original languageEnglish
Pages (from-to)1235-1241
Number of pages7
JournalJournal of the American Society for Mass Spectrometry
Volume20
Issue number7
DOIs
Publication statusPublished - Jul 1 2009

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ASJC Scopus subject areas

  • Structural Biology
  • Spectroscopy

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