Chiral differentiation of the noscapine and hydrastine stereoisomers by electrospray ionization tandem mass spectrometry. (January 2015)

• Record Type: Journal Article
• Authors: Nagy, Tibor; Kuki, Ákos; Antal, Borbála; Nagy, Lajos; Purgel, Mihály; Sipos, Attila; Nagy, Miklós; Zsuga, Miklós; Kéki, Sándor
• Is Part Of: Journal of mass spectrometry. Volume 50:Number 1(2015:Jan.)
• Page Start: 240
• Page End: 246
• Publication Date: 2015-01
• Subjects: Mass spectrometry -- Periodicals; 543.65
• DOI: 10.1002/jms.3527
• Languages: English
• ISSNs: 1076-5174

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>Energy‐dependent collision‐induced dissociation (CID) of the dimers [2 M + Cat]⁺ of the noscapine and hydrastine stereoisomers was studied where Cat stands for Li⁺, Na⁺, K⁺ and Cs⁺ ions. These dimers were generated '<italic>in situ</italic>' 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 ([2 M + Cat]⁺) was inversely proportional to the ionic radius of the cations. Furthermore, the structures of the dimers [2 M + Cat]⁺ were studied by high level quantum chemical calculations. Copyright © 2015 John Wiley &amp; Sons, Ltd.</p> </abstract>