High-performance liquid chromatographic separation of the enantiomers of unusual α-amino acid analogues

Antal Péter, Edit Olajos, Richard Casimir, Dirk Tourwé, Quirinus B. Broxterman, Bernard Kaptein, Daniel W. Armstrong

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

The direct and indirect stereochemical resolution of the enantiomers of ring- and α-methyl-substituted phenylalanines and phenylalanine amides was attempted by high-performance liquid chromatographic methods. The direct separation was carried out on two chiral stationary phases, the crown-ether- based Crownpak CR(+), and the teicoplanin-based Chirobiotic T, while the indirect resolution was performed by applying pre-column derivatization with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (GITC) and Nα- (2,4-dinitro-5-fluorophenyl)-L-alanine amide (Marfey's reagent, FDAA). The Chirobiotic T column was efficient in the separation of ring- and α-methyl- substituted phenylalanine analogues, but was ineffective for the amides of these analogues. The Crownpak CR(+) column separated the ring-substituted phenylalanines and amides, whereas the α-methylated analogues were coeluted. Of the two indirect methods, GITC derivatization seemed more effective than FDAA derivatization. (C) 2000 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)105-113
Number of pages9
JournalJournal of Chromatography A
Volume871
Issue number1-2
DOIs
Publication statusPublished - Feb 25 2000

Keywords

  • Amino acids
  • Enantiomer separation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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