L. Ye, A. Ramström, K. Mosbach
May 28, 1998
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Journal
Analytical Chemistry
Abstract
In this study, both diastereo- and enantioselective adsorbents for a dipeptide derivative were prepared using a molecular imprinting technique. The diastereo- and enantioisomers for the dipeptide derivative N-(benzyloxycarbonyl)aspartylphenylalanine methyl ester (ZAPM), in addition to the α- and β-isomers, were chosen as test compounds for the investigation of the imprinting effect. The close similarities between the structures of different isomers make it possible to interpret the roles of template structure on specific molecular recognition. A highly specific byproduct scavenger was prepared by simultaneously incorporating methacrylic acid and vinylpyridine as functional monomers. The binding selectivities of polymeric adsorbents for the α- and β-isomers are shown to be greatly enhanced by introducing enantiocomplementarities into the polymer matrixes. An anti-β-l,l-ZAPM polymer was applied in a solid-phase extraction protocol, for the purification of the product in the chemical synthesis of N-protected...