Published:Journal of Chromatographic Science,
ISSN 0021-9665Volume
38, Number 10, October 2000, pp. 430-434
Optical
Resolution of a Series of Potential Cholecystokinin Antagonist 4(3H)-Quinazolone
Derivatives by Chiral Liquid Chromatography on a1-Acid Glycoprotein Stationary
PhaseKrisztina
Gyimesi-Forrás*, György Szász, András Gergely, Mónika
Szabó, and József Kökösi
Institute of Pharmaceutical Chemistry, Semmelweis University H-1092 Budapest,
Högyes Endre u. 9., Hungary
Optical resolution
of the enantiomers of new 4(3H)-quinazolone derivatives is investigated using
the a1-acid glycoprotein chiral stationary phase (ChiraI-AGP). Stereoselective
separation of the model compounds can be controlled by varying the pH and adding
uncharged organic modifiers (acetonitrile and 2-propanol) to the mobile phase.
For the majority of quinazolone derivatives, ChiraI-AGP is proved to be an excellent
enantioselector, because optimized chromatographic conditions allow for the
baseline separation of the enantiomers. Separation factors between 1.19 and
1.85 are obtained. The effects of acetonitrile and 2-propanol on the chromatographic
behavior of the model compounds are quite different because of their different
hydrophobic- and hydrogen-bonding properties. The eluent pH and organic modifier
concentration also contributes to the chiral recognition by altering the protein
environment. The analysis of the experimental results leads to new information
about the chromatographic mechanism on a ChiraI-AGP surface.
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