Work

Design of Fast Redox-Controlled Self-Immolative Selenium-Based Cysteine Surrogates

Year: 2025

Type: article

Abstract: -selenoethyl cysteine derivatives into cysteine exhibits a strong Thorpe-Ingold effect. Notably, the gem-dimethyl substitution α to the selenium atom achieved rate accelerations up to 252-fold, enabling Cys unmasking through C-N bond cleavage within minutes. These investigations offer valuable insights into the mechanism of selenoethyl arm breakdown and new redox-sensitive Cys surrogates.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c01514

Authors: Eliott Roy, Vincent Diemer, Oleg Melnyk