Direct high-performance liquid chromatographic enantioseparation of β-methyl-substituted unusual amino acids on a quinine-derived chiral anion-exchange stationary phase

Antal Péter, Gabriella Török, Géza Tóth, Wolfgang Lindner

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A quinine-derived chiral anion-exchange stationary phase was used for the direct high-performance liquid Chromatographic separation of the enantiomers of the N-protected unusual β-substituted α-amino acids, β-methylphenylalanine, β-methyltyrosine, β-methyltryptophan, and β-methyl-l,2,3,4-tetrahydroisoquinoline-3-carboxylic acid. The readily prepared 2,4-dinitrophenyl and tert-butyloxycarbonyl derivatives were well separated, and in most cases the separation of all four stereoisomers of these β-methyl-α-amino acids could be obtained in one Chromatographic run. The elution sequences of the enantiomers of the different derivatives were determined and revealed a dependence on the type of the N-protecting group. In this context, the effects of different protecting groups (acetyl, tert-butyloxycarbonyl, benzoyl, 3,5-dinitrobenzoyl, benzyloxycarbonyl, 3,5-dinitrobenzyloxycarbonyl, 2,4-dinitrophenyl, and 9-fluorenylmethoxycarbonyl) on the Chromatographic behavior were investigated.

Original languageEnglish
Pages (from-to)628-636
Number of pages9
JournalJournal of separation science
Volume23
Issue number11
Publication statusPublished - Dec 1 2000

Keywords

  • Enantioseparation
  • High-performance liquid chromatography
  • Quinine-derived chiral stationary phase
  • β-methyl amino acids

ASJC Scopus subject areas

  • Analytical Chemistry
  • Filtration and Separation

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