Preparation of chitosan molecularly imprinted polymers and the recognition mechanism for adsorption of alpha-lipoic acid

Abstract

Two effective molecularly imprinted polymers for the adsorption of alpha-lipoic acid (ALA) were synthesized by the cross-linking of chitosan with epichlorohydrin (ECH) and glutaraldehyde (GLU), respectively, in the presence of ALA as template molecules. Investigations on the molar ratios of ALA and chitosan (–NH2) in the preparation of chitosan molecularly imprinted polymers (MIPs) were carried out with a factor of ALA rebinding capabilities. The surface morphology and chemical properties of the polymers were characterized. The optimized MIPs crosslinked by ECH (MIPs–ECH) and MIPs crosslinked by GLU (MIPs–GLU) had adsorption capabilities of 12.09 mg/g and 19.72 mg/g for ALA, respectively. The adsorption behaviors of two kinds of chitosan MIPs including adsorption kinetics and isotherms were investigated in detail. Adsorption and kinetic binding experiments showed that the prepared MIPs–ECH and MIPs–GLU had selective adsorption and excellent affinity for ALA. In addition, the possible binding models between ALA and chitosan oligosaccharide were predicted by molecular dynamics simulation.