One-step strategy for the synthesis of a derivatized cyclodextrin-based monolithic column

Abstract

Derivatized β-cyclodextrin (β-CD) functionalized monolithic columns were prepared by a "one-step" strategy using click chemistry. First, the intended derivatized β-CD monomers were synthesized by a click reaction between propargyl methacrylate and mono-6-azido-β-CD and then sulfonation or methylation was carried out. Finally, monolithic columns were prepared through a one-step in situ copolymerization of the derivatized β-CD monomer and ethylene glycol dimethacrylate. The sulfated β-CD-based monolith was successfully applied to the hydrophilic interaction liquid chromatography separation of nucleosides and small peptides, while the methylated β-CD-functionalized monolith was useful for the separation of nonpolar compounds and drug enantiomers in capillary reversed-phase liquid chromatography. The structures of the monomers were characterized by Fourier transform infrared spectroscopy and mass spectrometry. The physicochemical properties and column performance of monoliths were evaluated by scanning electron microscopy and micro high performance liquid chromatography. This strategy has considerable prospects for the preparation of other derivatized CD-functionalized methacrylate monoliths.

Keywords: Click chemistry; Derivatized β-cyclodextrin; Monolithic columns.