Issue 34, 2022

Effect of Na+ and K+ on the cucurbituril-mediated hydrolysis of a phenyl acetate

Abstract

The environment around the active site affects the catalytic activity of enzymes. Studying the cucurbit[7]uril-promoted acid hydrolysis of a cationic phenyl acetate derivative, we found that the hydrophobic cavity of the macrocycle screens the reaction centre from the positively charged neighbouring group. Moreover, the chelation of alkali metal cations with the cucurbit[7]uril portal and acetyl group of the substrate reduces the hydrolysis rate of the encapsulated ester in an aqueous solution. This type of inhibition corresponds to a rare uncompetitive model in contrast to the more common competitive model that relies on substrate displacement.

Graphical abstract: Effect of Na+ and K+ on the cucurbituril-mediated hydrolysis of a phenyl acetate

Supplementary files

Article information

Article type
Communication
Submitted
07 feb 2022
Accepted
31 mar 2022
First published
01 apr 2022
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2022,58, 5249-5252

Effect of Na+ and K+ on the cucurbituril-mediated hydrolysis of a phenyl acetate

N. Rad and V. Sashuk, Chem. Commun., 2022, 58, 5249 DOI: 10.1039/D2CC00772J

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