Molecularly imprinting of polymeric nucleophilic catalysts containing 4-alkylaminopyridine functions

Imidazole group of histidine residue is the essential catalytic group in the active site of a hydrolase protein. However, the imidazole is usually replaced with more nucleophilic 4-(N,N-dimethylamino)pyridines in organic syntheses. In order to introduce the supernucleophilic 4-dialkylaminopyridines into a catalytic site, a polymeric catalyst containing pyrrolidinopyridine moiety, is synthesized by imprinting of the bulk polymer with the transition state analogue of a substrate, accelerates the substrate-specific hydrolysis of p-nitrophenyl acetate. The results show that TSA-imprinted polymer containing 4-alkylaminopyridine groups is better than imidazole-appended polymer in artificial enzyme activity. (C) 2004 Elsevier Ltd. All rights reserved.