Selective Hydrolysis of Nonactivated Aryl Esters at pH 7 through Cooperative Catalysis

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.

Design and Synthesis of Metalloporphyrin Nanoconjugates for Dual Light-Responsive Antimicrobial Photodynamic Therapy

“…At this pH, the treatments of nanoconjugates tend to hydrolyze the ester bond between nanocomposites and metalloporphyrin. The nanoconjugates were suspended in NaOH solution and agitated (150 rpm) at 37 °C for 6 h, , followed by centrifugation at 15000 rpm for 20 min. The UV–vis spectrum of the supernatant layer was recorded to check for free metalloporphyrin.…”