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

被引：28

作者：

Gupta, Vinayak ^{[1
]}

Carroll, Kate S. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, Jupiter, FL 33458 USA

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 16期

关键词：

REDOX REGULATION; PROTEIN; INHIBITORS; OXIDATION; PROBES; CELLS;

D O I：

10.1039/c6cc00228e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：3414 / 3417

页数：4

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