Chiral separation of acidic compounds using an O-9-(tert-butylcarbamoyl)quinidine functionalized monolith in micro-liquid chromatography

J Chromatogr A. 2016 Apr 29:1444:64-73. doi: 10.1016/j.chroma.2016.03.047. Epub 2016 Mar 19.

Abstract

An O-9-(tert-butylcarbamoyl) quinidine (t-BuCQD) functionalized polymeric monolithic capillary column was prepared by the in situ copolymerization method. The physicochemical properties of the optimized monolithic column were characterized by scanning electron microscopy and micro-LC. Satisfactory column permeability, efficiency, stability and reproducibility were obtained for this monolithic column. The chiral recognition ability of the resulting monolith was also evaluated using 47 N-derivatized amino acids, eight N-derivatized dipeptides, and two herbicides. Under the selected conditions, the enantiomers of all chiral analytes were baseline separated with exceptionally high selectivity and resolution using micro-LC. It is worth noting that this chiral stationary phase (CSP) containing quinidine with a tert-butyl carbamate residue as chiral selector exhibits much higher enantioselectivity and diastereoselectivity than the previously developed O-9-[2-(methacryloyloxy)-ethylcarbamoyl]-10,11-dihydroquinidine (MQD) based CSP for N-derivatized amino acids and dipeptides. These results indicate that this novel quinidine-based polymeric monolith can be used as an effective tool for the enantioseparation of chiral acidic compounds.

Keywords: Chiral acids; Enantioseparation; Micro-LC; Monolith; Quinidine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry
  • Amino Acids / isolation & purification*
  • Chemistry Techniques, Analytical / methods*
  • Chromatography, Liquid*
  • Herbicides / isolation & purification
  • Microscopy, Electron, Scanning
  • Polymerization
  • Polymers / chemistry
  • Quinidine / analogs & derivatives
  • Quinidine / chemistry*
  • Reproducibility of Results
  • Stereoisomerism

Substances

  • Amino Acids
  • Herbicides
  • Polymers
  • tert-butylcarbamoylquinidine
  • Quinidine