Analysis of enantiomeric excess using mass spectrometry: fast atom bombardment/sector and electrospray ionization/Fourier transform mass spectrometric approaches

Yongjiang Liang; Jerald S Bradshaw; Reed M Izatt; R.Marshall Pope; David V Dearden

doi:10.1016/S1387-3806(98)14261-6

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Analysis of enantiomeric excess using mass spectrometry: fast atom bombardment/sector and electrospray ionization/Fourier transform mass spectrometric approaches

Journal article

Peer reviewed

Analysis of enantiomeric excess using mass spectrometry: fast atom bombardment/sector and electrospray ionization/Fourier transform mass spectrometric approaches

Yongjiang Liang, Jerald S Bradshaw, Reed M Izatt, R.Marshall Pope and David V Dearden

International journal of mass spectrometry, Vol.185, pp.977-988

1999

DOI: 10.1016/S1387-3806(98)14261-6

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Abstract

The utility of fast atom bombardment (FAB) ionization on a sector mass spectrometer, and of electrospray ionization (ESI) on a Fourier transform ion cyclotron resonance mass spectrometer, for enantiomeric excess measurements was explored. Both methods involved the same host–guest system: ( R, R)- or ( S, S)-dimethyldiketopyridino-18-crown-6 (host) and α-(1-naphthyl)ethylammonium (guest). Both use an achiral amine (benzylamine for the FAB experiments, cyclohexylamine for the ESI experiments) as an internal reference compound and involve competitive complexation of the achiral and chiral amines with the chiral host. The FAB experiments are shown to give stable, reproducible results, but exhibit a smaller degree of enantiodiscrimination than the ESI experiments. The ESI experiments, which involve measurement of apparent guest exchange equilibrium constants, show a linear relationship between apparent equilibrium constant and enantiomeric excess. The apparent equilibrium constant is shown to be a composition-weighted average of the equilibrium constants for the two pure enantiomers. Enantiomeric impurities as small as about 2% can currently be detected.

Chiral recognition

Enantiomer

Mass spectrometric determination

Optical purity

Details

Title: Subtitle: Analysis of enantiomeric excess using mass spectrometry: fast atom bombardment/sector and electrospray ionization/Fourier transform mass spectrometric approaches
Creators: Yongjiang Liang - Brigham Young University
Jerald S Bradshaw - Brigham Young University
Reed M Izatt - Brigham Young University
R.Marshall Pope - Brigham Young University
David V Dearden - Brigham Young University
Resource Type: Journal article
Publication Details: International journal of mass spectrometry, Vol.185, pp.977-988
Publisher: Elsevier B.V
DOI: 10.1016/S1387-3806(98)14261-6
ISSN: 1387-3806
eISSN: 1873-2798
Language: English
Date published: 1999
Academic Unit: Medicine Administration
Record Identifier: 9984627339002771

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