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Enantioseparations of ( R/S )-α-cyclohexylmandelic acid [( R/S )-CHMA] and methyl ( R/S )-α-cyclohexylmandelate [( R/S )-MCHMA] were performed on an achiral column (ODS) with 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) as a chiral mobile phase additive. The influences of chromatographic conditions on the retention behavior of ( R/S )-CHMA and ( R/S )-MCHMA were studied in detail. Meanwhile, the thermodynamics parameters of enantioseparations for ( R/S )-CHMA and ( R/S )-MCHMA were determined to discuss driven power in the enantioseparation process. The inclusion complexation of HP-β-CD with each enantiomer for ( R/S )-CHMA and ( R/S )-MCHMA was simulated by molecular docking to understand the chiral recognition mechanism of ( R/S )-CHMA and ( R/S )-MCHMA on HP-β-CD. The results showed that the chiral recognition ability of enantiometers of ( R/S )-CHMA and ( R/S )-MCHMA on HP-β-CD is better than α-CD, β-CD, γ-CD and DM-β-CD. Under the selected chromatographic conditions, baseline separations of enantiomers of ( R/S )-CHMA and ( R/S )-MCHMA were achieved. It is proved that the stoichiometry for ( R/S )-CHMA–HP-β-CD and ( R/S )-MCHMA–HP-β-CD complexes is 1:1. However, the results of thermodynamics parameters analysis and molecular modeling show that the enantioseparations of CHMA and MCHMA on HP-β-CD are enthalpy-driven processes and the primary driving forces responsible for chiral recognition are hydrophobic forces, dipole-dipole interaction, charge-transfer and hydrophobic interaction.

journal of chromatographic science

Enantioseparation and Chiral Recognition of α-Cyclohexylmandelic Acid and Methyl α-Cyclohexylmandelate on Hydroxypropyl-β-Cyclodextrin as Chiral Selector: HPLC and Molecular Modeling