A novel hydroquinidine imprinted microsphere using a chirality-matching N-Acryloyl-l-phenylalanine monomer for recognition of cinchona alkaloids

Using a combination of molecular imprinting technology and traditional chiral stationary phases, the synergistic effect between chiral monomer and chiral cavity of molecularly imprinted polymers in stereoselective recognition was investigated. We designed and synthesized an amino acid derivative to be used as a novel chiral functional monomer. Monodisperse molecularly imprinted core–shell microspheres using surface imprinting method on silica gel were prepared with hydroquinidine as the pseudo-template molecule for the resolution of cinchona alkaloids. The results showed a significant synergistic effect in stereoselective recognition, confirming our initial hypothesis. Furthermore, our computational simulation and experiments intensively support the hypothetical chiral recognition mechanism for the imprinted microspheres.

► Confirm the synergistic effect between chiral monomer and chiral cavity in enantioselective recognition.
► Designed and synthesized two novel chiral monomers and used the pseudo template.
► Computational simulation and experiments supports our proposed chiral recognition mechanism.