Photoswitchable Active Esters for the Control of Amide Bond Formation with Light.

ABSTRACT: Active esters are among the most utilized reagents for (bio)-materials functionalization via amide bond formation. To endow this type of ligation processes with spatiotemporal precision, we herein report the development of photoswitchable active esters, which toggle between poorly and highly reactive states upon irradiation with UV and visible light. Specifically, a dithienylethene photoswitch was introduced within the structure of common p-nitrophenyl active esters, whose electronic changes upon reversible open-closed photoisomerization turn on and off the activating effect of the p-nitro substituent on amidation reactivity. As a result, efficient light-induced modulation of amide bond formation kinetics was accomplished with these compounds, with their closed isomer exhibit

SUBMITTER: Villabona M 

PROVIDER: S-EPMC12569660 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature