Enantiomeric separation of unusual secondary aromatic amino acids

High-performance liquid chromatographic and gas chromatographic methods wer e developed for the separation of unusual secondary aromatic amino acids. A mino acids containing 1,2,3,4-tetrahydroisoquinoline, 1,2,3,4-tetrahydronor harmane-1-carboxylic acid and 1,2,3,4-tetrahydro-3-carboxy-2-carboline moie ties were synthetized in racemic or chiral forms. The highperformance liqui d chromatography was carried out either on a teicoplanin-containing chiral stationary phase or on an achiral C-18 column. In the latter case the diast ereomers of the amino acids formed by precolumn derivatization with the chi ral reagents 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate or 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide were separated. The gas chrom atographic analyses were based on separation on a Chirasil-L-Val column.