Enantiomeric resolution of primaquine, quinacrine and tafenoquine antibacterial medicines using ristocetin macrocyclic glycopeptide antibiotics CSP

Abstract

The enantiomeric resolution of primaquine, quinacrine and tafenoquine antibacterial medicines is described on Chirobiotc R column (150 ×4.6 mm, 5.0 µm). Two eluents used were methanol–acetonitrile-water-triethyl amine in the ratio of 70:10:20:0.1 (I) and 60:30:10:0.1 II) at 1.0 mL/min flow rate. The retention factors values for first and second enantiomers ranged from 1.0–3.40 and 3.40–5.40. The values of the separation and resolution factors were 1.59–3.40 and 2.10–2.50. In second solvent, only quinacrine could be resolved with 1.30 and 4.60 as a retention factor while the values of separation and resolution factors were 3.54 and 2.08. The supramolecular mechanism of the chiral resolution was established. The limits of detection and quantification ranged from 0.9–1.2 and 9.0–11.0 ng, respectively. The π-π interactions and hydrogen bondings were responsible for enantiomeric resolution. The enantiomeric method is useful for the chiral separation of primaquine, quinacrine, and tafenoquine antibacterial medicines.

Keywords

• chiral separation
• primaquine
• quinacrine & tafenoquine
• ristocetin macrocyclic glycopeptide antibiotics csp
• chiral recognition mechanism