Rapid nickel(ii)-promoted cysteine S-arylation with arylboronic acids
Rapid nickel(ii)-promoted cysteine S-arylation with arylboronic acids
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DOI：
10.1039/c9cc00159j
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发表时间：
2019-03-07
影响因子：
4.9
通讯作者：
Ball, Zachary T.
中科院分区：
文献类型：
--
作者：
Hanaya, Kengo;Ohata, Jun;Ball, Zachary T.
半胱氨酸残基的 S-芳基化是一种日益强大的蛋白质定点修饰工具，可提供新颖的结构和电子扰动。目前的工作展示了一种操作简单的半胱氨酸芳基化反应 2-硝基取代的芳基硼酸，由简单的镍 (ii) 盐促进。该过程在生理条件下的纯水介质中表现出惊人的快速反应速率，并且对半胱氨酸残基具有优异的选择性。天然蛋白质和肽的半胱氨酸芳基化允许连接有用的反应手柄，用于装订、成像或进一步缀合。
S-Arylation of cysteine residues is an increasingly powerful tool for site-specific modification of proteins, providing novel structure and electronic perturbation. The present work demonstrates an operationally-simple cysteine arylation reaction 2-nitro-substituted arylboronic acids, promoted by a simple nickel(ii) salt. The process exhibits strikingly fast reaction rates under physiological conditions in purely aqueous media with excellent selectivity toward cysteine residues. Cysteine arylation of natural proteins and peptides allows attachment of useful reactive handles for stapling, imaging, or further conjugation.