Application of a new chiral derivatizing agent to the enantioseparation of secondary amino acids.
A new chiral derivatizing agent, (S)-N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester, (S)-NIFE, was applied for the high-performance liquid chromatographic separation of enantiomers of 19 unnatural secondary amino acids: proline, pipecolic acid analogues, piperazine-2-carboxylic acid, morpholine-3-carboxylic acid, thiomorpholine-3-carboxylic acid and analogues containing the 1,2,3,4-tetrahydroisoquinoline, 1,2,3,4-tetrahydronorharmane, 1,2,3,4-tetrahydro-2-carboline and 2-benzazepine skeletons. Excellent resolutions were achieved for most of the investigated compounds by using a reversed-phase mobile phase system. The conditions of separation were optimized by variation of the mobile phase composition.
Péter
Antal
A
Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6720, Szeged, Hungary. apeter@chem.u-szeged.hu
Vékes
Erika
E
Tóth
Géza
G
Tourwé
Dirk
D
Borremans
Frans
F
D000596:Amino Acids / Q000032:analysis*; D002851:Chromatography, High Pressure Liquid; D004952:Esters / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D004952:Esters; D007202:Indicators and Reagents; C467080:N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester; D009574:Nitro Compounds