Semisynthesis of Ubiquitin and SUMO-Rhodamine 110-Glycine through Aminolysis of Boc-Protected Thioester Counterparts

作者：Jian Fan, Yinshan Ye, Guo‐Chao Chu, Zhongping Zhang, Yao Fu, Yi‐Ming Li, Jing Shi · 发表于：The Journal of Organic Chemistry · 年份：2019 · DOI：10.1021/acs.joc.9b01529 · 被引用次数：8 · 研究领域：Ubiquitin and proteasome pathways、Peptidase Inhibition and Analysis、Histone Deacetylase Inhibitors Research

Ubiquitin (Ub)-based fluorescent reagents are crucial to explore the activity of deubiquitinases (DUBs). Ub-Rho110-G is one of the preferred tools, whereas the current synthetic route is time-consuming. Here, we report a new semisynthetic strategy to produce Ub-Rho110-G through direct aminolysis of Boc-protected Ub-Mesna using bisglycyl-rhodamine 110. We also applied this strategy to synthesize active SUMO2-Rho110-G for the first time. Biochemical analysis demonstrated that semisynthetic Ub or SUMO-Rho110-G can be effectively used for the detection of the activity of DUBs or SUMO-specific enzymes.