Enantioseparation of ß2-amino acids by liquid chromatography using core-shell chiral stationary phases based on teicoplanin and teicoplanin aglycone

J Chromatogr A. 2021 Sep 13:1653:462383. doi: 10.1016/j.chroma.2021.462383. Epub 2021 Jul 5.

Abstract

Enantioseparation of nineteen ß2-amino acids has been performed by liquid chromatography on chiral stationary phases based on native teicoplanin and teicoplanin aglycone covalently bonded to 2.7 µm superficially porous silica particles. Separations were carried out in unbuffered (water/methanol), buffered [aqueous triethylammonium acetate (TEAA)/methanol] reversed-phase (RP) mode, and in polar-ionic (TEAA containing acetonitrile/methanol) mobile phases. Effects of pH in the RP mode, acid and salt additives, as well as counter-ion concentrations on chromatographic parameters have been studied. The structure of selectands (ß2-amino acids possessing aliphatic or aromatic side chains) and selectors (native teicoplanin or teicoplanin aglycone) was found to have a considerable influence on separation performance. Analysis of van Deemter plots and determination of thermodynamic parameters were performed to further explore details of the separation performance.

Keywords: kinetic and thermodynamic characterization, core-shell particles; liquid chromatography; macrocyclic glycopeptide-based chiral stationary phases; ß(2)-amino acids.

MeSH terms

  • Amino Acids* / isolation & purification
  • Chromatography, Liquid* / methods
  • Hydrogen-Ion Concentration
  • Solvents
  • Teicoplanin / analogs & derivatives*
  • Teicoplanin / chemistry

Substances

  • Amino Acids
  • Solvents
  • Teicoplanin
  • teicoplanin aglycone