Chiral Amines Derived from 2-Arylpropionic Acids: Novel Reagents for the Liquid Chromatographic (LC) Fluorescence Assay of Optically Active Carboxylic Acid Xenobiotics |
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Authors: | Spahn Hildegard Langguth Peter |
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Affiliation: | (1) Pharmakologisches Institut für Naturwissenschaftler der Johann Wolfgang Goethe-Universität, Theodor-Stern-Kai 7, Gebäude 75 A, D-6000 Frankfurt/Main 70, F.R.G;(2) Pharmakologisches Institut für Naturwissenschaftler, Theodor-Stern-Dai 7, Gebäude 75 A, D-6000 Frankfurt/Main 70, F.R.G.;(3) Pharmazeutisches Institut, Abteilung Galenik, Eidgenössische, Technische Hochschule, Clausiusstrae 25, CH-8092 Zürich, Switzerland |
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Abstract: | For the enantiospecific analysis of optically active carboxylic acids, the availability of readily detectable coupling components is desirable, but highly fluorescent chiral amines are rare. From activated enantiomers of fluorescent 2-arylpropionic acids fluorescent chiral amines were synthesized via Curtius degradation, i.e., under formation of the acyl azide, the isocyanate, and finally, the amine. The formation of isocyanates and of amine hydrochlorides led to an inversion of the direction of rotation of polarized light. Amines derived from R- and S-flunoxaprofen, R- and S-naproxen, and R/S-benoxaprofen were characterized. The amines were found to be applicable for the chiral separation of carboxylic acids (such as 2-arylpropionic acids) as diastereomeric derivatives via high-performance liquid-chromatographic (normal and reversed-phase) and thin-layer chromatographic techniques. |
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Keywords: | chiral derivatization nonsteroidal antirheumatic drugs 2-arylpropionic acids naproxen flunoxaprofen benoxaprofen |
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