N-[4-(6-Methoxy-2-benzoxazolyl)]benzoyl-l-amino Acids as Chiral Derivatization Reagents for Amine Enantiomers

Autor: Kondo, Junichi, Imaoka, Toshi, Suzuki, Nobuyuki, Kawasaki, Takao, Nakanishi, Akio, Kawahara, Yukinori
Zdroj: Analytical Sciences; October 1994, Vol. 10 Issue: 5 p697-703, 7p
Abstrakt: N-[4-(6-Methoxy-2-benzoxazolyl)]benzoyl-l-phenylalanine (BOX-l-Phe) and N-[4-(6-methoxy-2-benzoxazolyl)]benzoyl-l-proline (BOX-l-Pro) have been synthesized to permit separation of amine enantiomers by high-performance liquid chromatography. Enantiomeric amines were readily condensed with the chiral derivatization reagents in the presence of 2,2′-dipyridyl disulfide and triphenylphosphine. The diastereomeric BOX-l-Pro amides were separable by both normal-phase and reversed-phase chromatography. They could be sensitively detected fluorometrically at 432 nm, with excitation at 325 nm in the reversed-phase mode. The detection limit of the BOX-l-Pro derivative of R-1-(1-naphthyl)ethylamine was 30 fmol at a signal-to-noise ratio of 3.
Databáze: Supplemental Index