Cyclodextrin clicked chiral stationary phases with functionalities-tuned enantioseparations in high performance liquid chromatography

J Chromatogr A. 2015 Aug 7:1406:342-6. doi: 10.1016/j.chroma.2015.06.051. Epub 2015 Jun 25.

Abstract

In this work, two cyclodextrin (CD) chiral stationary phases (CSPs) have been developed by clicking per-4-chloro-3-methylphenylcarbamoylated mono-6(A)-azido-β-CD (CSP1) and per-5-chloro-2-methylphenylcarbamoylated mono-6(A)-azido-β-CD (CSP2) onto alkynylated silica support. The enantioslectivies of the as-obtained new CSPs have been evaluated using 29 model racemates including aromatic alcohols, flavonoids, β-blocker and FMOC-amino acids in both reversed-phase (RP) and normal-phase (NP) high performance liquid chromatography (HPLC). The CD functionalities tuned enantioselectivities were elucidated in different HPLC elution modes. Higher chiral resolutions were achieved in RP-elution mode with the aid of the inclusion complexation in comparison to NP-elution mode. The π-π stacking interaction and dipole-dipole interaction provided by phenylcarbamate moieties can also contribute to the enantioseparation.

Keywords: Chiral stationary phase; Click chemistry; Cyclodextrin; Enantioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry
  • Amino Acids / chemistry
  • Chromatography, High Pressure Liquid*
  • Click Chemistry
  • Cyclodextrins / chemistry*
  • Flavonoids / chemistry
  • Silicon Dioxide / chemistry
  • Stereoisomerism

Substances

  • Alcohols
  • Amino Acids
  • Cyclodextrins
  • Flavonoids
  • Silicon Dioxide