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

A. 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

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Enantiomers
Phenylalanine
Amides
Crown Ethers
Teicoplanin
Amino Acids
Liquids
Alanine
isothiocyanic acid
phenylalanine amide
chirobiotic T
phenylalanine methyl ester
Marfey's reagent

Keywords

  • Amino acids
  • Enantiomer separation

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

High-performance liquid chromatographic separation of the enantiomers of unusual α-amino acid analogues. / Péter, A.; Olajos, Edit; Casimir, Richard; Tourwé, Dirk; Broxterman, Quirinus B.; Kaptein, Bernard; Armstrong, Daniel W.

In: Journal of Chromatography A, Vol. 871, No. 1-2, 25.02.2000, p. 105-113.

Research output: Contribution to journalArticle

Péter, A, Olajos, E, Casimir, R, Tourwé, D, Broxterman, QB, Kaptein, B & Armstrong, DW 2000, 'High-performance liquid chromatographic separation of the enantiomers of unusual α-amino acid analogues', Journal of Chromatography A, vol. 871, no. 1-2, pp. 105-113. https://doi.org/10.1016/S0021-9673(99)00889-4
Péter, A. ; Olajos, Edit ; Casimir, Richard ; Tourwé, Dirk ; Broxterman, Quirinus B. ; Kaptein, Bernard ; Armstrong, Daniel W. / High-performance liquid chromatographic separation of the enantiomers of unusual α-amino acid analogues. In: Journal of Chromatography A. 2000 ; Vol. 871, No. 1-2. pp. 105-113.
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