Xiao Hua, Xiaona Han, Rong Ji, Pincheng Li, Yu Wang, Yanyan Guo, Jing Shi
{"title":"Flexible Semi-synthesis of UFM11–82–Propargylamine by Aminolysis with Valine–Propargylamine","authors":"Xiao Hua, Xiaona Han, Rong Ji, Pincheng Li, Yu Wang, Yanyan Guo, Jing Shi","doi":"10.1021/acs.orglett.4c04546","DOIUrl":null,"url":null,"abstract":"We report a novel semi-synthetic strategy of UFM1<sub>1–82</sub>–propargylamine by N–S acyl transfer to give UFM1<sub>1–80</sub>R thioester and subsequent aminolysis with valine–propargylamine. The use of the valine–propargylamine molecule overcomes the inability of the valine site to efficiently undergo the N–S acyl transfer. This strategy benefits from the availability of raw materials for bulk expression, and the resulting probe shows high selectivity toward UFM1-specific proteases in buffers and cell lysates.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"77 2 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04546","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
We report a novel semi-synthetic strategy of UFM11–82–propargylamine by N–S acyl transfer to give UFM11–80R thioester and subsequent aminolysis with valine–propargylamine. The use of the valine–propargylamine molecule overcomes the inability of the valine site to efficiently undergo the N–S acyl transfer. This strategy benefits from the availability of raw materials for bulk expression, and the resulting probe shows high selectivity toward UFM1-specific proteases in buffers and cell lysates.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
