Optimization of the separation of enantiomers of basic drugs retention mechanisms and dynamic modification of the chiral bonding properties on a α1-acid glycoprotein column

Liquid Chromatographic Resolution of Fendiline and Its Analogues on a Chiral Stationary Phase Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid

“…Analogue (7) containing a propyl group instead of the methyl group at the chiral center of fendiline was also prepared to see the effect of the methyl group on the chiral resolution. Analogues (8)(9)(10)(11)(12) containing ortho-substituted phenyl or 1-naphthyl group and analogues (13)(14)(15)(16)(17) containing para-substituted phenyl or 2-naphthyl group instead of the simple phenyl group were prepared for the purpose of elucidating the role of the phenyl group at the chiral center of fendiline in the chiral recognition. For the resolution of secondary amino compounds on CSP 1, mobile phase composition has been known to be very important.…”

“…To find out the most widely applicable mobile phase condition for the resolution of fendiline and its analogues, we selected five analytes including fendiline and its analogues 8, 12, 13 and 17. Analytes 8 and 12 were selected to represent analogues (8)(9)(10)(11)(12) containing ortho-substituted phenyl or 1-naphthyl group and analytes 13 and 17 were selected to represent analogues (13)(14)(15)(16)(17) containing para-substituted phenyl or 2-naphthyl group instead of the simple phenyl group at the chiral center of fendiline. The selected five analytes were resolved on CSP 1 with the variation of the mobile phase composition.…”

“…However, liquid chromatographic enantioseparation of fendiline on CSPs is quite rare. Only a CSP based on α1-acid glycoprotein (AGP) was used for the enantioseparation of fendiline by liquid chromatography [16]. CSPs based on chiral crown ethers were very successful in the determination of enantiomeric composition of chiral compounds containing a primary amino group [12,[17][18][19].…”

“…Fendiline also contains a secondary amino group and, in this instance, it is expected to be resolved on CSP 1. In this study, we wish to report the resolution of fendiline and its analogues (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) shown in Figure 2 on CSP 1.…”

New data on the sorption properties of ?1-acid glycoprotein chiral stationary phase

“…4 Because of its broad applicability and the use of buffered aqueous mobile phases being compatible with biological fluids, the CHIRAL-AGP column has become popular for the direct separation of the different types of enantiomers (e.g., acidic, neutral, and basic drugs). [5][6][7] Owing to the highly complex structure of the protein, the character of the chiral binding processes is only incompletely known and the choice of conditions for stereoselective separation is more or less empirical. 8,9 The organic modifiers have primarily been introduced to decrease the retention times of the highly retained analytes, but in many cases they influence the chiral selectivity as well.…”