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Issue 16, 2016
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Rational design of reversible and irreversible cysteine sulfenic acid-targeted linear C-nucleophiles

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Abstract

Concerns about off-target effects has motivated the development of reversible covalent inhibition strategies for targeting cysteine. However, such strategies have not been reported for the unique cysteine oxoform, sulfenic acid. Herein, we have designed and identified linear C-nucleophiles that react selectively with cysteine sulfenic acid. The resulting thioether adducts exhibit reversibility ranging from minutes to days under reducing conditions, showing the feasibility of tuning C-nucleophile reactivity across a wide range of time scales.

Graphical abstract: Rational design of reversible and irreversible cysteine sulfenic acid-targeted linear C-nucleophiles

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Article information


Submitted
10 Jan 2016
Accepted
24 Jan 2016
First published
25 Jan 2016

Chem. Commun., 2016,52, 3414-3417
Article type
Communication
Author version available

Rational design of reversible and irreversible cysteine sulfenic acid-targeted linear C-nucleophiles

V. Gupta and K. S. Carroll, Chem. Commun., 2016, 52, 3414
DOI: 10.1039/C6CC00228E

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