Selective Hydrolysis of Nonactivated Aryl Esters at pH 7 through Cooperative Catalysis
1Department of Chemistry, Iowa State University, Ames, Iowa 50011-3111, United States.
Abstract:
Most reported artificial esterases only hydrolyze highly activated substrates. We here report synthetic catalysts that hydrolyze nonactivated aryl esters at pH 7, via cooperative action of a thiourea group that mimics the oxyanion hole of a serine protease and a nearby nucleophilic/basic pyridyl group. The molecularly imprinted active site distinguishes subtle structural changes in the substrate, including elongation of the acyl chain by two carbons or shift of a remote methyl group by one carbon.
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