Cysteine-based chiral selectors for the ligand-exchange separation of amino acids

J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Nov 1;875(1):108-17. doi: 10.1016/j.jchromb.2008.06.007.

Abstract

Three cysteine-based coated selectors, S-benzyl-(R)-cysteine, S-diphenylmethyl-(R)-cysteine and S-trityl-(R)-cysteine, have been used in the ligand-exchange separation of a selected set of natural and unnatural underivatized amino acids. With only few exceptions, a gain in enantiodiscrimination was obtained when the most lipophilic discriminating agent, characterized by the presence of a trityl moiety, was engaged. Moreover, a new descriptive structure-separation relationship study through molecular surface (Jurs) and shape (Shadow) descriptors provided evidence that specific physico-chemical features of the employed chiral selector result decisive in establishing which property of the analyte is responsible for the enantiorecognition accomplishment.

Publication types

  • Comparative Study
  • Validation Study

MeSH terms

  • Amino Acids / isolation & purification*
  • Chemical Fractionation / methods
  • Chromatography, High Pressure Liquid / instrumentation
  • Chromatography, High Pressure Liquid / methods*
  • Cysteine / analogs & derivatives*
  • Cysteine / chemistry
  • Ligands
  • Reproducibility of Results
  • Stereoisomerism

Substances

  • Amino Acids
  • Ligands
  • Cysteine