A rapid, qualitative thin-layer chromatographic method for the separation of the enantiomers of unusual aromatic amino acids

Z. Darula, Gabriella Török, G. Wittmann, Els Mannekens, Koen Iterbeke, Géza Tóth, Dirk Tourwé, A. Péter

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

A rapid thin-layer chromatographic (TLC) method has been developed for the separation and purity control of the enantiomers of several unusual aromatic amino acids (phenylalanine, tyrosine, histidine, and tryptophan analogs, and analogs containing tetralin or 1,2,3,4-tetrahydroisoquinoline skeletons) synthesized in racemic or homochiral form. The compounds were analyzed on Macherey-Nagel Chiralplate TLC plates with acetonitrile-methanol- water, 4 + 1 + 1 or 4 + 1 + 2 (v/v) or acetonitrile-methanol-water- diisopropylethylamine, 4 + 1 + 2 + 0.1 (v/v) as mobile phase. The compounds were visualized with ninhydrin. Good separation and reliable results were usually obtained. The configurations of the asymmetric centers of the investigated amino acids were determined either by use of enantiomerically pure amino acids as standards or by use of enzymes, e.g. α-chymotrypsin, Lamino acid oxidase or carboxypeptidase A. By this method the configurations of unnatural amino acids built into peptides can also be determined after hydrolysis of the peptides.

Original languageEnglish
Pages (from-to)346
Number of pages1
JournalJournal of Planar Chromatography - Modern TLC
Volume11
Issue number5
Publication statusPublished - Sep 1998

Fingerprint

Aromatic Amino Acids
Enantiomers
Amino Acids
Methanol
Carboxypeptidases A
Ninhydrin
Peptides
Water
Chymotrypsin
Phenylalanine
Histidine
Skeleton
Tryptophan
Tyrosine
Hydrolysis
Oxidoreductases
Acids
Enzymes
acetonitrile

Keywords

  • Chiralplate
  • Enantiomeric separation
  • Thin-layer chromatography
  • Unusual aromatic amino acids

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

A rapid, qualitative thin-layer chromatographic method for the separation of the enantiomers of unusual aromatic amino acids. / Darula, Z.; Török, Gabriella; Wittmann, G.; Mannekens, Els; Iterbeke, Koen; Tóth, Géza; Tourwé, Dirk; Péter, A.

In: Journal of Planar Chromatography - Modern TLC, Vol. 11, No. 5, 09.1998, p. 346.

Research output: Contribution to journalArticle

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