An acrylamide-based molecularly imprinted polymer for the efficient recognition of optical amino acid hydantoins

Abstract

Using acrylamide as a hydrogen bonding functional monomer and (5R)-5-benzylhydantoin as a template, a molecularly imprinted polymer was prepared in a polar solvent, which exhibited good enantiomeric recognition properties. The binding selectivity of the polymer was evaluated by batch methods. Scatchard analyses showed that two classes of binding sites were produced in the imprinted polymer and their dissociation constants were estimated to be (4.6 ± 0.8) × 10^–5 and (1.3 ± 0.2) × 10^–4 mol L^–1, respectively. This was in agreement with the prediction of the binding characteristics of the polymer by a spectrophotometric method. Study of the effect of water on the separation factor of the polymer further proved that the hydrogen bonding interactions played an important role in the recognition of acrylamide-based molecularly imprinted polymers.