Chiral resolution of diphenylalanine by high-performance liquid chromatography on a crown-ether-based chiral stationary phase and by NMR spectroscopy

W. Lee; E. Bang; W. Lee

doi:10.1007/BF02492541

Chiral resolution of diphenylalanine by high-performance liquid chromatography on a crown-ether-based chiral stationary phase and by NMR spectroscopy

W. Lee, E. Bang, W. Lee

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8 Citations (Scopus)

Abstract

The enantiomers of diphenylalanine (DPA) were well separated by chiral HPLC and NMR spectroscopy on the chiral stationary phase (CSP) derived from (18-crown-6)-2,3,11,12-tetracarboxylic acid (18-C-6-TA). The chromatographic parameters such as separation factors and retention times were greatly influenced by the mobile phase conditions. The (+)-18-C-6-TA used in the CSP was also employed as a chiral solvating agent for the enantiodiscrimination of the DPA enantiomers by NMR spectroscopy. The proton of the DPA analyte showing the chemical shift nonequivalences was used in determining the enantiomeric composition of the analyte.

Original language	English
Pages (from-to)	457-461
Number of pages	5
Journal	Chromatographia
Volume	57
Issue number	7-8
DOIs	https://doi.org/10.1007/BF02492541
Publication status	Published - 2003 Apr 1

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All Science Journal Classification (ASJC) codes

Analytical Chemistry
Biochemistry
Clinical Biochemistry
Organic Chemistry

Cite this

Lee, W., Bang, E., & Lee, W. (2003). Chiral resolution of diphenylalanine by high-performance liquid chromatography on a crown-ether-based chiral stationary phase and by NMR spectroscopy. Chromatographia, 57(7-8), 457-461. https://doi.org/10.1007/BF02492541

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AB - The enantiomers of diphenylalanine (DPA) were well separated by chiral HPLC and NMR spectroscopy on the chiral stationary phase (CSP) derived from (18-crown-6)-2,3,11,12-tetracarboxylic acid (18-C-6-TA). The chromatographic parameters such as separation factors and retention times were greatly influenced by the mobile phase conditions. The (+)-18-C-6-TA used in the CSP was also employed as a chiral solvating agent for the enantiodiscrimination of the DPA enantiomers by NMR spectroscopy. The proton of the DPA analyte showing the chemical shift nonequivalences was used in determining the enantiomeric composition of the analyte.

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10.1007/BF02492541