Liquid chromatographic enantiomer separation of amino acid esters as 9-anthraldimine schiff bases using polysaccharide-derived chiral stationary phases

Hu Huang, Jing Yu Jin, Joon Hee Hong, Wonjae Lee, Hyo Kyung Han, Jong Seong Kang

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

The liquid chromatographic enantiomer separation of several amino acid methyl esters as 9-anthraldehyde Schiff base derivatives on coating and covalently bonded polysaccharide-derived chiral stationary phases (CSPs) is described. The 9-anthraldehyde imine derivatives of amino acid esters were readily prepared by stirring 9-anthraldehyde with the amino acid ester hydrochloride salts. The performance of Chiralcel OD among all examined CSPs was superior to that of the other CSPs for resolution of 9-anthraldimine derivatives of amino acid methyl esters. The enantiomers of all examined amino acid methyl esters as the 9-anthraldimine derivatives were base-line resolved on Chiralcel OD. The L-enantiomers of all analytes are preferentially retained on Chiralcel OD. The chromatographic methods developed in this study were applied in the determination of enantiomeric purity of some commercially available D- or L-amino acid methyl esters.

Original languageEnglish
Pages (from-to)209-216
Number of pages8
JournalJournal of Liquid Chromatography and Related Technologies
Volume34
Issue number3
DOIs
StatePublished - Jan 2011

Keywords

  • 9-anthraldimine derivative
  • amino acid ester
  • chiral stationary phase
  • enantiomer separation

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