A single-step preparation of carbohydrate functionalized monoliths for separation and trapping of polar compounds

J Chromatogr A. 2020 Sep 27:1628:461481. doi: 10.1016/j.chroma.2020.461481. Epub 2020 Aug 16.

Abstract

A single-step copolymerization strategy was developed for the preparation of carbohydrate (glucose and maltose) functionalized monoliths using click reaction. Firstly, novel carbohydrate-functionalized methacrylate monomers were synthesized through Cu(I)-catalyzed 1,3-dipolar cycloaddition (alkyne-azide reaction) of terminal alkyne with azide of carbohydrate derivatives. The corresponding carbohydrate functionalized monolithic columns were then prepared through a single-step in-situ copolymerization. The physicochemical properties and performance of the fabricated monolithic columns were evaluated using scanning electron microscopy, Fourier-transform infrared spectroscopy, and nano-liquid chromatography. For the optimized monolithic column, satisfactory column permeability and good separation performance were demonstrated for polar compounds including nucleoside, phenolic compounds and benzoic acid derivatives. The monolithic column is also highly useful for selective and efficient enrichment of glycopeptides from human IgG tryptic digests. This study not only provided a novel hydrophilic column for separation and selective trapping of polar compounds, but also proposed a facile and efficient approach for preparing carbohydrate functionalized monoliths.

Keywords: Carbohydrate functionalized monolith; Click chemistry; Single-step preparation.

MeSH terms

  • Carbohydrates / chemical synthesis
  • Carbohydrates / chemistry*
  • Click Chemistry / methods*
  • Glycopeptides / chemistry
  • Humans
  • Hydrophobic and Hydrophilic Interactions
  • Polymerization
  • Polymethacrylic Acids / chemical synthesis
  • Polymethacrylic Acids / chemistry
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • Carbohydrates
  • Glycopeptides
  • Polymethacrylic Acids
  • polymethacrylic acid