Abstract
The enantiomers of the bronchodilator terbutaline were separated by reversed-phase high performance liquid chromatography after derivatization with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate(GITC) reagent. The derivatization proceeded quantitatively within 1 h at room temperature. The corresponding diastereomeric thiourea derivatives were well resolved on an ODS column with acetonitrile-acetate buffer as a mobile phase. Elution orders of the diastereomers were confirmed by derivatization of R-(−)-terbutaline and S-(+)-terbutaline which were collected by semi-preparative chiral HPLC using Sumichiral OA-4700 column. The native fluorescence of terbutaline was quenched by derivatization with GITC. The detection limit was 25ng when monitored at UV 278 nm.
Similar content being viewed by others
References
Borgström, L., Nyberg, L., Jonsson, S., Lindberg, C. and Paulson, J., Pharmacokinetic evaluation in man of terbutaline given as separate enantiomers and as the racemate.Br. J. Clin. Pharmacol., 27, 49–56(1989).
Handley, D. A., McCullough, S. D., Crowther, S. D. and Morley, J., Sympathomimetic enantiomers and athma.Chirality, 10, 262–272(1998).
Jeppson, A. B., Johansson, K. and Waldeck, B., Steric aspects of agonism and antagonism at β-adrenoceptors: Experiments with the enantiomers of terbutaline and pindolol.Acta Pharmacol. Toxicol., 54, 285–291 (1984).
Kallstrom, B. L., Sjoberg, J. and Waldeck, B., Steric aspects of formoterol and terbutaline: is there an adverse effect of the distomer on airway smooth muscle function..Chirality, 8, 567–573(1996).
Kinoshita, T., Kasahara, T. and Nimura, N., Reversed-phase high-performance liquid chromatographic resolution of non-esterified enantiomeric amino acids by derivatization with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate and 2,3,4-ttri-O-acetyl-α-D-arabinopyranosyl isothiocyanate.J. Chromatogr., 210, 77–81 (1981).
Nimura, N., Toyama, A. and Kinoshita, T., Optical resolution of amino acid enantiomers by high-performance liquid chromatography.J. Chromatogr., 316, 547–552 (1984).
Sedman, A. J. and Gal, J., Resolution of the enantiomers of propanolol and other beta-adrenergic antagonists by high-performance liquid chromatography.J. Chromatogr., 278, 199–203 (1983).
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.Biomed. Chromatogr., 6, 163–167 (1992).
Walle, T. and Walle, U. K., Stereoselective sulfate conjugation of racemic terbutaline by human liver cytosol.Br. J. Clin. Pharmacol., 30, 127–133 (1990).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kim, K.H., Kim, D.S., Hong, SP. et al. Reversed-phase high performance liquid chromatographic separation of the enantiomers of terbutaline by derivatization with 2,3,4,6-tetra-o-acetyl-β-D-glucopyranosyl isothiocyanate. Arch Pharm Res 23, 26–30 (2000). https://doi.org/10.1007/BF02976461
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02976461