Chiral separation of β-blockers after derivatization with (-)-menthyl chloroformate by reversed-phase high performance liquid chromatography

Archives of Pharmacal Research

Volumn 22, Issue 6, 1999, Pages 608-613

  Kim, Kyeong Ho ^a   Choi, Pok Wha ^a   Hong, Seon Pyo ^b   Kim, Hyun Ju ^a  

^a Kangwon National University   (South Korea)

^b Kyung Hee University   (South Korea)

Author keywords

( ) Menthyl chloroformate; Chiral derivatization; Resolution; Blocker

Indexed keywords

ACETONITRILE; ACETONITRILE DERIVATIVE; BETA ADRENERGIC RECEPTOR BLOCKING AGENT; FORMIC ACID DERIVATIVE; MENTHYL CHLOROFORMATE; METHANOL; WATER;

ARTICLE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOISOMERISM; TIME;

ACETONITRILES; ADRENERGIC BETA-ANTAGONISTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FORMATES; METHANOL; STEREOISOMERISM; TIME FACTORS; WATER;

EID: 0033252208     PISSN: 02536269     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02975333     Document Type: Article

References (17)

1. Bhatti, M. M. and Foster, R. T., Stereospecific high-performance liquid chromatographic assay of metoprolol., J. Chromatogr., 579, 361-365 (1992).
2. 1-acid glycoprotein-based chiral stationary phase. J. Chromatogr. A, 760, 193-203 (1997).
3. Chassaing, C., Thienpont, A. and Felix, G., Regioselective carbamoylated and benzoylated cellulose for the separation of enantiomers in high-perpormance liquid chromatography. J. Chromatogr. A, 738, 157-167 (1996).
4. Ekelund, J., Arkens, A. V., Kirsten, B.-H., Fich, K., Olsen, L. and Petersen, P. V., Chiral separations of β-blocking drug substances using chiral stationary phases. J. Chromatogr. A, 708, 253-261 (1995).
5. 1-acid glycoprotein column. J. Chromatogr. A, 694, 57-69 (1995).
6. Huynh, N.-H., Karlsson, A. and Pettersson, C., Enantiomeric separation of basic drugs using N-benzyloxycarbonylglycyl-L-proline as counter ion in methanol. J. Chromatogr. A, 705, 275-287 (1995).
7. Mehvar, R., Liquid chromatographic analysis of Atenolol enantiomers in human plasma and urine. J. Pharm. Sci., 78, 1035-1039 (1989).
8. Mehvar, R., Stereospecific liquid chromatographic analysis of racemic adrenergic drugs utilizing precolumn derivatization with (-)-menthyl chloroformate., J. Chromatogr., 493, 402-408 (1988).
9. Nakamura, K., Fujima, H. and Kitagawa, H., Preparation and chromatographic characteristics of a chiral-recognizing perphenylated cyclodextrine column. J. Chromatogr. A, 694, 111-118 (1995).
10. Nathanson, J. A., Stereospecificity of beta adrenergic antagonists; r-enantiomers show increased selectivity for beta-2 receptors in ciliary process. J. Pharmcol. Exp. Ther., 245, 94-98 (1988).
11. Pflugmann, G., Spahn, H. and Mutschler, E., Determination of mrtoprolol enantiomers in plasma and urine using (S)-(-)-phenylethyl isothiocyanate as a chiral reagent. J. Chromatogr., 421, 161-164 (1987).
12. Schmitthenner, H. F., Fedorchuk, M. and Walter, D. J., Resolution of antihypertensive aryloxypropanolamine enantimers by reversed- phase chromatography of (-)-menthyl chloroformate derivatives. J. Chromatogr., 487, 197-203 (1989).
13. Schuster, D., Modi, M. W., Lalka, D. and Gengo, F. M., Reversed-phase high performance liquid chromatographic assay to quantitate diastereomeric derivatives of metoprolol enantiomers in plasma., J. Chromatogr., 433, 318-325 (1988).
14. Srinivas, N. R. and Igwemezie, L. N., Chiral Separation by High Perpormance Liquid Chromatography. I. Review on Indirect Separation of Enantiomers as Diastereomeric Derivatives Using Ultraviolet, Fluorescence and Electrochemical Detection. Biomedical Chromatography, 6, 163-167 (1992).
15. Veigl, E., Bohs, B., Mandle, A., Krametter, D. and Lindner, W., Evaluation of silica gel-based brush type chiral cation exchangers with S-N-(3,5-dinitrobenzoyl) tyrosine as chiral selector: attempt to interpret the discouraging results. J. Chromatogr. A, 694, 151-161 (1995).
16. Welch, C. J. and Perrin, S. R., Improved chiral stationary phase for β-blocker enantioseparations. J. Chromatogr. A, 690, 218-225 (1995).
17. Witte, D. T., Bosman, J., Boer, T. D., Drenth, B. F. H., Ensing, K. and Zwwuw, R. A. D., Influence of chemical structure of tricyclic tertiary dimethylamines on chiral separation by reversed-phase high-performance liquid chromatography after derivatization with (-)-menthylchloroformate. J. Chromatogr., 553, 365-372 (1991).