Differentiation of lisinopril and its RSS diastereomer by liquid chromatography combined with collision‐induced dissociation mass spectrometry

Abstract

A simple and sensitive liquid chromatography tandem multiple-stage mass spectrometry (HPLC/MS/MS) method suitable for bulk lisinopril analysis was developed, by which lisinopril and its RSS isomer were separated and differentiated. In the collision-induced dissociation (CID) mass spectra of the [M + H](+) ions, the abundance of the fragment ion of m/z 246 for lisinopril was about two times higher than the ion of m/z 245; however, the former fragment ion was noted to be a little lower than the latter for RSS isomer at all collision energies. In the CID mass spectra of the [M + Li](+) ion, the abundance of the rearrangement ion of m/z 315 for the RSS isomer was about three times higher than that for lisinopril. Furthermore, the difference was supported by the results of energy-resolved mass spectrometry (ERMS) in the test range of collision energies. Similar differences were also observed between the CID mass spectra of lisinopril and RSS isomer methylester, which indicated that the RSS isomer could be rapidly characterized by the CID mass spectra of both the protonated and lithium adduct ion. Elemental compositions of all the ions were confirmed by Fourier Transform ion cyclotron resonance ESI mass spectrometry (FT-ICR-ESI/MS). In addition, theoretical computations were carried out to support the experimental results.

Screening and quantitative analysis of antioxidants in the fruits of Livistona chinensis R. Br using HPLC-DAD–ESI/MS coupled with pre-column DPPH assay

“…HPLC-MS n has been confirmed to be an ideal tool for analyzing the natural plant secondary metabolites, owing to that it can provide affluent multistage fragment information for compounds with collision-induced dissociation (Chen, He, Mao, Sun, & Pan, 2009;Chen, Li, Sun, Pan, & Schlunegger, 2008a;Sun, Wu, & Pan, 2009;Sun, Zhu, Hu, Wang, & Pan, 2010). Therefore, in our study, high performance liquid chromatography-photo diode array detectionelectrospray ionization tandem mass spectrometry (HPLC-DAD/ ESI-MS n ) technique was employed to identification of the antioxidative components in L. chinensis fruits.…”

Gas Phase Chemistry of Li+with Amides: the Observation of LiOH Loss in Mass Spectrometry

“…In the past few decades, continuous efforts have been devoted to the investigation of the dissociation reactions of charged compounds derived from protonation [4][5][6][7][8] or deprotonation [9][10][11][12][13]. On the other hand, the mass spectrometric fragmentations of metal cationized, especially lithiated biomolecules, have attracted much attention because of the desire to measure intrinsic metal ion affinity and identify the binding sites [14,15], and because the interesting dissociation pathways exhibited by these compounds are usually different from the protonated and deprotonated analogues [16,17]. Recently, the fragmentation behaviors of lithiated species have been reported for peptides, fatty acids, phospholipids, polytetrahydrofuran, cardiolipins, thioesters, cholesteryl esters, and disaccharides [18][19][20][21][22][23][24][25][26].…”

Formation of [M + 15]+ ions from aromatic aldehydes by use of methanol: in-source aldolization reaction in electrospray ionization mass spectrometry

“…Thirdly, it is interesting that the relative abundances of the ions [M + H] + and [M + 15] + can be affected by the positional patterns of a substituent. Although isomers share exactly the same mass, they can sometimes be distinguished solely by MS methods because of the different fragmentation behavior of their structurally diagnostic ions under the same conditions . Taking methoxybenzaldehyde as an example, the three positional isomers can be distinguished by breakdown curves (Fig.…”