Relationship between enantioselectivity of alternative molecularly imprinted polymeric membranes and species of amino acid residues composing chiral recognition sites.
Molecularly imprinted polymeric membranes with tetrapeptide residue H-Asp(OcHex)-Asp(OcHex)-Asp(OcHex)-Asp(OcHex)-CH2- (DDDD) or H-Glu(OBzl)-Glu(OBzl)-Glu(OBzl)-Glu(OBzl)-CH2- (EEEE) were prepared during membrane preparation (casting) processing in the presence of print molecules. The Boc-L-Trp imprinted polymeric membranes thus obtained showed adsorption selectivity toward Ac-L-Trp from its racemic mixtures. From adsorption isotherms of Ac-Trp, the chiral recognition site, that had been formed by the presence of print molecules in the membrane preparation process, exclusively recognized Ac-L-Trp that possessed the same configuration of the print molecule. The affinity constants between chiral recognition sites in the membrane and Ac-L-Trp was determined to be 1.00 x 10(4) mol(-1) dm3 and 1.08 x 10(4) mol(-1) dm3 for the DDDD and EEEE membranes, respectively. Enantioselective electrodialysis could be attained by applying an optimum potential difference to give permselectivity, with a value close to its adsorption selectivity.
Yoshikawa
M
M
Department of Polymer Science and Engineering, Kyoto Institute of Technology, Matsugasaki, Kyoto 606-8585, Japan.
Kondo
Y
Y
Morita
Y
Y
D000596:Amino Acids / Q000737:chemistry*; D008567:Membranes, Artificial; D011108:Polymers / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D008567:Membranes, Artificial; D011108:Polymers