可逆和不可逆的半胱氨酸亚磺酸靶向线性碳亲核试剂的合理设计。
Rational design of reversible and irreversible cysteine sulfenic acid-targeted linear C-nucleophiles.
作者信息
Gupta Vinayak, Carroll Kate S
机构信息
Department of Chemistry, The Scripps Research Institute, Jupiter, Florida 33458, USA.
出版信息
Chem Commun (Camb). 2016 Feb 25;52(16):3414-7. doi: 10.1039/c6cc00228e.
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.
摘要
对脱靶效应的担忧推动了针对半胱氨酸的可逆共价抑制策略的发展。然而，尚未有针对独特的半胱氨酸氧化形式——亚磺酸的此类策略的报道。在此，我们设计并鉴定了与半胱氨酸亚磺酸选择性反应的线性C-亲核试剂。所得硫醚加合物在还原条件下表现出从几分钟到几天不等的可逆性，表明在广泛的时间尺度上调节C-亲核试剂反应性的可行性。
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