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Reference type: Journal
Authors: Yoshikawa M, Izumi J
Article Title: Chiral recognition sites converted from tetrapeptide derivatives adopting racemates as print molecules.
Publication date: 2003
Journal: Macromolecular Bioscience
Volume: 3
Issue: (9)
Page numbers: 487-498.
DOI: 10.1002/mabi.200350016

Abstract: Molecularly imprinted polymeric membranes were prepared from polystyrene resin bearing tetrapeptide derivatives H- Asp(OcHex)-Leu-Asp(OcHex)-Glu(OBzl)-OCH2- (DLDE) consisting of D-amino acid residues or L-amino acid residues. The tetrapeptide derivatives were converted into chiral recognition sites by using not only an optically pure Boc-Trp but also racemic Boc-Trps as a print molecule. The chiral recognition ability depends on the combination of the absolute configuration of the print molecule and that of constituting amino acid residues. The membrane prepared from a DLDE derivative consisting of D-amino acid residues and imprinted by Boc-D-Trp recognized the D-isomer in preference to the corresponding L-isomer and vice versa. In the present study, it was also made clear that racemic print molecules were effective in generating chiral recognition sites. The affinity constant of the generated chiral recognition site was determined to be 9.6 x 103 mol(-1).dm(3), which was independent of the molecular imprinting conditions. Enantioselective permeation was attained by applying electrodialysis. An optimum permselectivity of 5.9, which corresponds to the adsorption selectivity, was attained

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