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Enantiomeric Separation Of Unusual Secondary Aromatic Amino Acids, A. Péter, G. Török, G. Tóth, W. Van Den Nest, G. Laus, D. Tourwé, Daniel W. Armstrong
Enantiomeric Separation Of Unusual Secondary Aromatic Amino Acids, A. Péter, G. Török, G. Tóth, W. Van Den Nest, G. Laus, D. Tourwé, Daniel W. Armstrong
Chemistry Faculty Research & Creative Works
High-performance liquid chromatographic and gas chromatographic methods were developed for the separation of unusual secondary aromatic amino acids. Amino acids containing 1,2,3,4-tetrahydroisoquinoline, 1,2,3,4-tetrahydronorharmane-1-carboxylic acid and 1,2,3,4-tetrahydro-3-carboxy-2-carboline moieties were synthetized in racemic or chiral forms. The high-performance liquid chromatography was carried out either on a teicoplanin-containing chiral stationary phase or on an achiral C18 column. In the latter case the diastereomers of the amino acids formed by precolumn derivatization with the chiral reagents 2,3,3,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate or 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide were separated. The gas chromatographic analyses were based on separation on a Chirasil-L-Val column.