Enantioseparation in high performance liquid chromatography: preparation and evaluation of a vancomycin-based chiral stationary phase via surface-initiated atom transfer radical polymerization

Abstract

A chromatographic technique based on a chiral stationary phase (CSP) has been explored for enantioseparation. Herein, poly(glycidyl methacrylate) (poly(GMA)) brushes were grafted on the surface of silica gel via surface-initiated atom transfer radical polymerization (SI-ATRP), followed by the introduction of vancomycin as a chiral selector. The as-synthesized material was characterized by elemental analysis, scanning electron microscopy (SEM), Fourier transform infrared (FT-IR) and thermogravimetric analysis (TGA), proving the formation of vancomycin-immobilized brushes. Then the resulting CSP was explored to separate 7 racemic drugs (bicalutamide, 1-benzyl-5-phenylbarbituric acid, chlorpheniramine maleate, fluoxetine hydrochloride, verapamil hydrochloride, benzoxazocine hydrochloride and isoprenaline hydrochloride) in high performance liquid chromatography (HPLC). Several factors affecting the enantioseparation performance of the vancomycin-immobilized CSP, including the triethylamine (TEA) content in the buffer, pH value, content of organic solvent in the mobile phase, flow rate and injection volume, were mainly optimized. Under the optimal conditions, baseline separation of fluoxetine hydrochloride (R_S = 2.52) was achieved, which was better than that on a commercial Chirobiotic V column, while enantioseparation of bicalutamide (R_S = 1.01), chlorpheniramine maleate (R_S = 0.77), 1-benzyl-5-phenylbarbituric acid (R_S = 0.67), isoprenaline hydrochloride (R_S = 0.73), verapamil hydrochloride (R_S = 0.91) and benzoxazocine hydrochloride (R_S = 1.03) was partly achieved. It was concluded that SI-ATRP is a robust way to fabricate vancomycin-based CSPs for enantioseparation.