Chiral Discrimination of Drugs by DNA Tetranucleotides under Electrospray Ionisation Conditions

Abstract

The DNA tetranucleotides, extended versions of GCA at the 3'-end or 5'-end, were used as chiral selectors for the chiral discrimination of atenolol, DOPA, tamsulosin, valacyclovir and zolmitriptan. Chiral discrimination was achieved by investigating the collision-induced dissociation spectra of the [X+Y-2H](2-) ion generated by electrospraying a solution mixture of tetranucleotide (X) and R- or S-analyte drug (Y). The relative abundances of the precursor ion and the product ion, resulting from the loss of drug, were considered for measuring the degree of chiral discrimination. Among all the tetranucleotides studied, AGCA showed the highest chiral discrimination. The present study emphasised the position of an adenine base in the tetranucleotide in chiral discrimination. The suitability of the method for the measurement of optical purity was also demonstrated in the case of zolmitriptan.

Enantiomeric differentiation of β-amino alcohols under electrospray ionization mass spectrometric conditions

“…Although innumerable studies covered the enantiomeric differentiation of amino acids applying the mass spectrometry methods, only a few studies described the enantiomeric differentiation of chiral drugs with amino alcohol functionality. There were some reports in the literature covering on the enantiomeric differentiation of drugs possessing amino alcohol functionality under ESI conditions . Jeminet et al .…”

“…There were some reports in the literature covering on the enantiomeric differentiation of drugs possessing amino alcohol functionality under ESI conditions. [20,21] Jeminet et al reported the differentiation of enantiomeric phenylglycinol. [22] However, there is no systematic study on a series of β-amino alcohols derived from natural amino acids.…”

Differentiation of enantiomeric drugs by iodo‐substituted L‐amino acid references under electrospray ionization mass spectrometric conditions

“…The CR value obtained for atenolol in the current study is higher than that of previous reports, while the value obtained for propranolol is comparable to that reported ( Table 1). [29,34] The CID spectra of the trimeric adduct ion obtained from enantiomers of atenolol are shown in Fig. 2.…”

“…demonstrated the enantiomeric differentiation of DOPA using the fixed ligand method by selecting different biphenylic compounds as the fixed ligand . Recently, we reported differentiation of a set of chiral drugs by employing DNA tetranucleotide as the reference compound …”

“…[33] Recently, we reported differentiation of a set of chiral drugs by employing DNA tetranucleotide as the reference compound. [34] In all the aforementioned reports, a different chiral selector was applied for each drug. Use of a single reference that differentiates enantiomers for a broad range of compounds including drugs is ideal, but so far there are no such reports in the literature.…”