Rapid and efficient chiral separation of nateglinide and its L-enantiomer on monolithic molecularly imprinted polymers

A monolithic molecularly imprinted polymer (monolithic MIP) was designed and prepared for chiral separation of nateglinide and its L-enantiomer. The enantiomers were rapidly separated on this novel monolithic MIP based chiral stationary phase (MIP-CSP), whereas the enantioseparation was not obtained on the non-imprinted polymer (NIP). Chiral recognition was found to be dependent on the stereo structures and the arrangement of functional groups of the imprinted molecule and the cavities on MIP. Thermodynamic data (Delta Delta H and Delta Delta S) obtained by Van't Hoff plots revealed an enthalpy-controlled enantioseparation. The binding capacity was evaluated by frontal analysis. Monolithic nateglinide-MIP had an effective number of binding sites B-t = 41.15 mu mol g(-1) with a dissociation constant of K-d = 7.40 mM. The morphological characteristics of the monolithic MIP were investigated by pore analysis and scanning electron microscope (SEM). Results showed that both mesopores and macropores were formed in the monolith. Over all, this study presents a new and practical possibility for providing high rates of mass transfer, fast separations and high efficiencies without the pressure constraints of the traditional bulk molecularly imprinted polymers, through the monolithic MIPs. (c) 2005 Elsevier B.V. All rights reserved.