Insights into self-degradation of cysteine esters and amides under physiological conditions yield new cleavable chemistry.

Abstract

An unprecedented H2S release from cysteine esters and amides (CysO/NHR) under physiological conditions was discovered and the plausible mechanism was proposed. Alkylation of the amino moiety of cysteine esters enables the H2S release to be tuned and further provides support to the mechanistic insights. This discovery not only provides new insights into several fundamental science issues including non-enzymatic H2S-produced pathways, but also inspires new tunable cleavable motifs for sustained release of arylthiols and even for prodrug design.