Chiral differentiation of the noscapine and hydrastine stereoisomers by electrospray ionization tandem mass spectrometry

Tibor Nagy, Ákos Kuki, Borbála Antal, Lajos Nagy, Mihály Purgel, Attila Sipos, Miklós Nagy, M. Zsuga, S. Kéki

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Energy-dependent collision-induced dissociation (CID) of the dimers [2M+ Cat]+ of the noscapine and hydrastine stereoisomers was studied where Cat stands for Li+, Na+, K+ and Cs+ ions. These dimers were generated 'in situ' from the electrosprayed solution. The survival yield (SY) method was used for distinguishing the noscapine and hydrastine dimers. Significant differences were found between the characteristic collision energies (CE50, i.e. the collision energy necessary to obtain 50% fragmentation) of the homo- (R,R; S,S) and heterochiral (R,S; S,R) stereoisomers. To distinguish the enantiomer pairs L-, D-tyrosine ([M+ Tyr + Cat]+) and L-, D-lysine ([M+ Lys + Cat]+) were used as chiral selectors. Furthermore, these heterodimers [M + amino acid + Cat]+ were also applied to determine the stereoisomeric composition. It was found that the characteristic collision energy (CE50) of the noscapine and hydrastine homodimers ([2M+ Cat]+) was inversely proportional to the ionic radius of the cations. Furthermore, the structures of the dimers [2M+ Cat]+ were studied by high level quantum chemical calculations.

Original languageEnglish
Pages (from-to)240-246
Number of pages7
JournalJournal of Mass Spectrometry
Volume50
Issue number1
DOIs
Publication statusPublished - Jan 19 2015

Fingerprint

Noscapine
Electrospray ionization
Stereoisomerism
Electrospray Ionization Mass Spectrometry
cats
Tandem Mass Spectrometry
Dimers
Mass spectrometry
Cats
mass spectroscopy
ionization
dimers
collisions
Enantiomers
Lysine
Tyrosine
Cations
Amino acids
Positive ions
selectors

Keywords

  • Chiral differentiation
  • Chiral mass spectrometry
  • Hydrastine
  • Noscapine
  • Stereoisomers
  • Survival yield

ASJC Scopus subject areas

  • Spectroscopy
  • Medicine(all)

Cite this

Chiral differentiation of the noscapine and hydrastine stereoisomers by electrospray ionization tandem mass spectrometry. / Nagy, Tibor; Kuki, Ákos; Antal, Borbála; Nagy, Lajos; Purgel, Mihály; Sipos, Attila; Nagy, Miklós; Zsuga, M.; Kéki, S.

In: Journal of Mass Spectrometry, Vol. 50, No. 1, 19.01.2015, p. 240-246.

Research output: Contribution to journalArticle

Nagy, Tibor ; Kuki, Ákos ; Antal, Borbála ; Nagy, Lajos ; Purgel, Mihály ; Sipos, Attila ; Nagy, Miklós ; Zsuga, M. ; Kéki, S. / Chiral differentiation of the noscapine and hydrastine stereoisomers by electrospray ionization tandem mass spectrometry. In: Journal of Mass Spectrometry. 2015 ; Vol. 50, No. 1. pp. 240-246.
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