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The Pharmaceutical Society of Korea (대한약학회)
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Chiral Separation of ${\beta}-Blockers$ after Derivatization with a New Chiral Derivatization Agent, GATC

  • Published : 2006.11.30
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Abstract

A new chiral derivatization agent with sugar moiety, 2,3,4,6-tetra-O-acetyl-${\beta}$-D-galactopyranosyl isothiocyanate (GATC) was synthesized. Several ${\beta}-blockers$ were investigated for the possible separation of the enantiomers by reversed-phase HPLC after derivatization with this new chiral derivatization agent (GATC). GATC was reacted readily with ${\beta}-blockers$ at room temperature and the reaction mixture could directly be injected into the HPLC system. The corresponding diastereomers were well resolved on an ODS column with acetonitrile-ammonium acetate buffer as a mobile phase and monitored at UV 254 nm. The optimization of the derivatization procedure (concentration of GATC, reaction temperature and time) and HPLC conditions (pH and ionic strength of mobile phase) were investigated and compared with GITC.

Keywords

References

  1. Baimer, K., Lagerstrom, P. O., and Persson, B. A., Reversed retention order and other stereoselective effects in the separation of amino alcohols on Chiralcel OD. J. Chromatogr., 592, 331-337 (1992) https://doi.org/10.1016/0021-9673(92)85104-2
  2. Boppana, V. K., Geschwindt, L., Cyronak, M. J., and Rhodes, G., Determination of th enantiomers of fenoldopam in human plasma by reversed-phase high-performance liquid chromatography after chiral derivatization. J. Chromatogr., 592, 317- 322 (1992) https://doi.org/10.1016/0021-9673(92)85102-Y
  3. Kim, K. H., Choi, P. W., Hong, S. P., and Kim, H. J., Chiral separation of ${\beta}$-blockers after derivatization with (-)-menthyl chloroformate by reversed-phase high-performance liquid chromatography. Arch. Pharm. Res., 22, 608-613 (1999) https://doi.org/10.1007/BF02975333
  4. Lanchote, V. L., Bonato, P. S., Cerqueira, P. M., Pereira, V. A., and Cesarino, E. J., Enantioselective analysis of metoprolol in plasma using high-performance liquid chromatographic direct and indirect separations: application in pharmacokinetics, J. Chromatogr., B., 738, 27-37 (2000) https://doi.org/10.1016/S0378-4347(99)00476-4
  5. Nishi, H., Fujimura, N., Yamaguchi, H., and Fukuyama, T., Reversed-phase HPLC separation of enantiomers of denopamine after derivatization with GITC chiral reagent. Chromatographia, 30, 186-190 (1990) https://doi.org/10.1007/BF02274544
  6. Peter, M., Peter, A., and Fulop, F., Development of new isothiocyanate-based chiral derivatizing agent for amino acids. Chromatographia, 50, 373-375 (1999) https://doi.org/10.1007/BF02490845
  7. Srinivas, N. R. and Igwemezie, L. N., Chiral separation by High performance liquid chromatography. I. Review on indirect separation of enantiomers as diastereomeric derivatives using ultraviolet, fluorescence and electrochemical detection. Biomedical chromatography, 6, 163-167 (1992) https://doi.org/10.1002/bmc.1130060402
  8. Tian, Z., Hrinyo-pavlina, T., and Roeske, R. W., Resolution of 2,3,4,6-tetra-O-acetyl-${\beta}$-D-glucopyranosyl isothiocyanate derivatives of ${\alpha}$-methyl amino acid enantiomers by highperformance liquid chromatography. J. Chromatogr., 541, 297-302 (1991) https://doi.org/10.1016/S0021-9673(01)96001-7