Chromatographic methods for monitoring the optical isomers of unusual aromatic amino acids

• Published in: Journal of Chromatography A Vol. 797; no. 1-2; pp. 165 - 176
• Main Authors: Péter, Antal, Török, Gabriella, Tóth, Géza, Van Den Nest, Wim, Georges Laus, Tourwé, Dirk
• Format: Journal Article Conference Proceeding
• Language: English
• Published: Amsterdam Elsevier B.V 27.02.1998; Elsevier
• Subjects: Amino acids; Analytical chemistry; Chemistry; Chromatographic methods and physical methods associated with chromatography; Exact sciences and technology; Other chromatographic methods; Amino acids; Enantiomer separation; Electron impact; Separation; Nitrogen heterocycle; Coupled method; HPLC chromatography; Chiral stationary phase; Derivatization; Direct method; Gas chromatography; α-Aminoacid; Ultraviolet detector; Position isomer; Indirect method; Optical resolution; Enantiomer; Bicyclic compound; Benzenic compound; Aromatic compound; Mass spectrometry
• ISSN: 0021-9673
• DOI: 10.1016/S0021-9673(97)00967-9

Unusual aromatic amino acids (phenylalanine, tyrosine and tryptophan analogues, and analogues containing tetraline, 1,2,3,4-tetrahydroisoquinoline or 1,2,3,4-tetrahydro-2-carboline skeletons) were synthesized in racemic or chiral form. The enantiomers of these unusual aromatic amino acids were separated by different chromatographic methods. The gas chromatographic analyses were based on separation on a Chirasil-L-Val column, using N-trifluoroacetyl-isobutyl esters of amino acids, while high-performance liquid chromatography was carried out either on a Crownpak CR(+) chiral column, or on an achiral column for the separation of diastereomeric derivatives formed with 1-fluoro-2,4-dinitrophenyl-5-l-alanine amide or 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate.