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

Chem Commun (Camb)

State Key Laboratory of Organic-Inorganic Composites and Beijing Key Lab of Bioprocess, Beijing University of Chemical Technology (BUCT), Beijing 100029, China.

Published: April 2023

An unprecedented HS 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 HS 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 HS-produced pathways, but also inspires new tunable cleavable motifs for sustained release of arylthiols and even for prodrug design.

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http://dx.doi.org/10.1039/d3cc00684kDOI Listing

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