Sa. Piletsky et al., Combined hydrophobic and electrostatic interaction-based recognition in molecularly imprinted polymers, MACROMOLEC, 32(3), 1999, pp. 633-636
Molecularly imprinted polymers selective for D- and L-phenylalanine have be
en prepared in water solution using 2-acryloylamido-2,2'-dimethylpropane su
lfonic acid and bisacryloyl beta-cyclodextrin as functional monomers, and N
,N'-diacryloylpiperazine as cross-linker. Polymer-ligand recognition was ev
aluated using a combination of HPLC, displacement chromatography and fluore
scence spectroscopic studies. HPLC studies revealed that the imprinted poly
mers possess optimal ligand selectivity in 30% water solution in acetonitri
le. The results demonstrate that a balance of hydrophobic and electrostatic
interactions is required for ligand recognition by these polymers. The imp
rinting effect is sufficiently strong to reverse the inherent chiral select
ivity of the cyclodextrin molecule.