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Paper | Regular issue | Vol 65, No. 5, 2005, pp.1111-1120
Published online, 1st March, 2005
DOI: 10.3987/COM-05-10346
High-Performance Liquid Chromatographic Enantioseparation Based on Diastereomer Formation with New Fluorescent Chiral Quinoxalines

Akira Katoh,* Ryoji Yamamoto, Takeshi Fujimoto, and Ryota Saito

*Department of Applid Chemistry, Faculty of Engineering, Seikei University, Musashino-shi, Tokyo 180-8633, Japan

Abstract

Two kinds of chiral 2,3-dimorpholinoquinoxalines bearing L-proline and N-bromoacetylproline residues at C-6 position were newly synthesized. The derivatization of (±)-naproxen, (±)-ibuprofen, and (±)-2-phenylpropionic acid with chiral quinoxalines afforded the diastereomers, which emitted an intense fluorescence. All the diastereomers were clearly separated within 16 min on reversed-phase (Finepak SIL C18S) HPLC equipped with a fluorescence detector. The detection limit of the derivatized product was estimated to be 5 pmol/10μL injection volume at S/N=5. Further, the quantum yield of the diastereomer was estimated to be 0.052 by using the relative quantum yield measurement with anthracene as a standard.