Synthesis and chromatographic evaluation of phenyl/tetrazole bonded stationary phase based on thiol-epoxy ring opening reaction

J Sep Sci. 2018 Feb;41(4):856-867. doi: 10.1002/jssc.201701125. Epub 2018 Jan 16.

Abstract

A silica-based reversed-phase stationary phase bonding with phenyl and tetrazole groups was synthesized by thiol-epoxy ring opening reaction. The bonded groups could not only provide hydrophobic interaction, but also π-π, hydrogen bonding, electrostatic interactions, and so on. The results of characterization with elemental analysis and solid-state 13 C cross-polarization magic-angle-spinning NMR spectroscopy indicated the successful preparation of phenyl/tetrazole sulfoether bonded stationary phase. Chromatographic evaluation revealed that phenyl/tetrazole sulfoether bonded stationary phase behaved well under the reversed-phase mode. The column parameters (H, S*, A, B, and C) showed different selectivity compared with some typical commercial columns, and it was validated by the separation of estrogen, ginsenoside, alkaloid samples. Based on the different selectivity between phenyl/tetrazole sulfoether bonded stationary phase and C18 columns, phenyl/tetrazole sulfoether bonded stationary phase also showed potential to construct a 2D reversed-phase liquid chromatography system with C18. And it was verified by the separation of corydalis tuber and curcuma zedoary extracts.

Keywords: reversed-phase liquid chromatography; stationary phases; thiol-epoxy ring opening reaction; traditional Chinese medicine; two-dimensional liquid chromatography.

MeSH terms

  • Chromatography, Liquid
  • Epoxy Compounds / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Silicon / chemistry
  • Spectrophotometry, Infrared
  • Sulfhydryl Compounds / chemistry*
  • Tetrazoles / chemical synthesis*
  • Tetrazoles / chemistry*

Substances

  • Epoxy Compounds
  • Sulfhydryl Compounds
  • Tetrazoles
  • 1H-tetrazole
  • 1-phenyl-5-mercaptotetrazole
  • Silicon