Summary
Ligand-exchange micellar electrokinetic chromatography has been used for the simultaneous separation of 16 positional and optical isomers of the tryptophan family. The Cu(II) complex with L-hydroxyproline was used as the chiral selector. Two groups of anionic surfactant, linear alkylbenzenesulfonates (LAS) and straight-chain alkyl sulfates such as sodiumn-decyl sulfate (SDeS), sodium dodecyl sulfate (SDS) and sodiumn-tetradecyl sulfate (STS), were used for simultaneous separation. The best result was obtained by use of SDS. The influence of SDS concentration and of pH on the separation was investigated. The separation behavior in the absence of the Cu(II) complex with L-hydroxyproline was also examined. Use of organic modifiers causes the resolution to decrease. Relationships between the logarithm of the octanol-water partition coefficient (logP OW) and resolution, and between logP OW and migration time are discussed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
B. Chankyetadze, Capillary Electrophoresis in Chiral Analysis, John Wiley & Sons, Chichester, UK, 1997.
M. Warner, Anal. Chem.66, 1137A (1994).
R. Crossley, Chirality and Biological Activity of Drugs, CRC Press, Boca Raton, FL, 1995.
E. J. Ariens, in E. J. Ariens, W. Soudijin, and P. B. M. W. Timmermans (Editors), Stereochemistry and Biological Activity of Drugs, Blackwell, Oxford, 1983, p. 11.
V. A. Davankov, S. V. Rogozhin, J. Chromatogr.60, 280 (1971).
S. V. Rogozhin, V. A. Davankov, Chem. Commun. 490 (1971).
E. Gassmann, J. E. Kuo, R. N. Zare, Science230, 813 (1985).
P. Gozel, E. Gassmann, H. Michelsen, R. N. Zare, Anal. Chem.59, 44 (1987).
A. S. Cohen, A. Paulus, B. L. Karger, Chromatographia24, 15 (1987).
C. Desiderio, Z. Aturki, S. Fanali, Electrophoresis15, 864 (1994).
M. G. Schmid, F. Gubitz, Enantiomer1, 23 (1996).
S. Terabe, K. Otsuka, K. Ichikawa, A. Tsuchiya, T. Ando, Anal. Chem.56, 111 (1984).
S. Terabe, K. Otsuka, T. Ando, Anal. Chem.57, 834 (1985).
P. G. Muijselaar, K. Otsuka, S. Terabe, J. Chromatogr. A780, 41 (1997).
M. G. Khaledi, J. Chromatogr. A780, 3 (1997).
Z. Chen, J.-M. Lin, K. Uchiyama, T. Hobo, J. Chromatogr. A813, 369 (1998).
S. Yang, M. Khaledi, Anal. Chem.67, 499 (1995).
S. Takeda, S. Wakida, M. Yamane, K. Higashi, S. Terabe, J. Chromatogr. A781, 11 (1997).
B. J. Herbert, J. G. Dorsey, Anal. Chem.67, 744 (1995).
On-line logP calculation by Interactive LOGKOW Demo in http://esc.syrres.com/ESC/≈kowint.htm.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Chen, Z., Lin, J.M., Uchiyama, K. et al. Simultaneous separation of sixteen positional and optical isomers of the tryptophan family by ligand-exchange micellar electrokinetic chromatography. Chromatographia 49, 436–443 (1999). https://doi.org/10.1007/BF02467620
Received:
Revised:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02467620