One-pot preparation of glutathione-silica hybrid monolith for mixed-mode capillary liquid chromatography based on "thiol-ene" click chemistry

J Chromatogr A. 2014 Aug 15:1355:228-37. doi: 10.1016/j.chroma.2014.06.023. Epub 2014 Jun 12.

Abstract

A novel glutathione (GSH)-silica hybrid monolithic column synthesized via a combination of thiol-ene click reaction and one-pot process was described, where thiol-end GSH organic monomer and 2,2-azobisisobutyronitrile (AIBN) were mixed with hydrolyzed tetramethyloxysilane (TMOS) and γ-methacryloxypropyltrimethoxysilane (γ-MAPS) and then introduced into a fused-silica capillary for simultaneous polycondensation and "thiol-ene" click reaction to form the GSH-silica hybrid monolith. The effects of the molar ratio of TMOS/γ-MAPS, the amount of GSH, and the volume of porogen on the morphology, permeability and pore properties of the prepared GSH-silica hybrid monoliths were studied in detail. A uniform monolithic network with high porosity was obtained. A series of test compounds including alkylbenzenes, amides, and anilines were used to evaluate the retention behaviors of the GSH-silica hybrid monolithic column. The results demonstrated that the prepared GSH-silica hybrid monolith exhibited multiple interactions including hydrophobicity, hydrophilicity, as well as cation exchange interaction. The run-to-run, column-to-column and batch-to-batch reproducibilities of the GSH-silica hybrid monolith for phenols' retention were satisfactory with the relative standard deviations (RSDs) less than 1.3% (n=5), 2.6% (n=3) and 3.2% (n=3), respectively, indicating the effectiveness and practicability of the proposed method. In addition, the GSH-silica hybrid monolith was applied to the separation of nucleotides, peptides and protein tryptic digests, respectively. The successful applications suggested the potential of the GSH-silica hybrid monolith in complex sample analysis.

Keywords: Capillary liquid chromatography; Click chemistry; Glutathione; Mixed-mode; One-pot; Organic–inorganic hybrid monolith.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid / instrumentation
  • Chromatography, High Pressure Liquid / methods*
  • Click Chemistry / instrumentation
  • Click Chemistry / methods*
  • Glutathione / chemistry*
  • Hydrophobic and Hydrophilic Interactions
  • Methacrylates / chemistry
  • Microscopy, Electron, Scanning
  • Peptides / isolation & purification
  • Proteins / isolation & purification
  • Silanes / chemistry
  • Silicon Dioxide / chemistry*
  • Sulfhydryl Compounds / chemistry

Substances

  • Methacrylates
  • Peptides
  • Proteins
  • Silanes
  • Sulfhydryl Compounds
  • methacryloxypropyltrimethoxysilane
  • Silicon Dioxide
  • Glutathione