Abstract: Separations using molecularly imprinted polymers (MIPs) which mimic biological interactions are reported. Multiple hydrogen bonding interactions between nucleotide bases play a crucial role in stabilizing the structure of double-stranded DNA. A novel functional monomer designed to form multiple hydrogen bonds with barbiturate templates has been synthesized and used for molecular imprinting. Liquid chromatographic analysis shows that a cyclobarbital-imprinted polymer possesses a distinct preference for the template molecule. Another example which mimics the interactions between peptide bonds in -helical or -sheet domains of proteins is introduced. A MIP which utilizes a L-valine derivative as a functional monomer is shown to exhibit stereoselectivity for a number of dipeptides