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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

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Carbonic anhydrase mimics with rationally designed active sites for fine-tuned catalytic activity and selectivity in

Foroogh Bahrami¹, Yan Zhao¹

¹Department of Chemistry, Iowa State University Ames Iowa 50011-3111 USA zhaoy@iastate.edu +1 515 294 0105 +1 515 294 5845.

Catalysis Science & Technology

|November 28, 2023

Abstract:

Numerous hydrolytic enzymes utilize zinc as a cofactor for catalysis. We here report water-soluble polymeric nanoparticles with zinc ions in active sites and a nearby base as a mimic of carbonic anhydrase (CA). Their pK_a of 6.3-6.4 for zinc-bound water is lower than the 6.8-7.3 value for natural enzymes, which allows the catalyst to hydrolyze nonactivated alkyl esters under neutral conditions-a long sought-after goal for artificial esterases. The size and shape of the active site can be rationally tuned through a template used in molecular imprinting. Subtle structural changes in the template, including shifting an ethyl group by one C-N bond and removal of a methylene group, correlate directly with catalytic activity. A catalyst can be made to be highly specific or have broad substrate specificity through modular synthesis of templates.

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