首次实现tRNA摆动核苷的有机催化非对映选择性合成：（）-和（）-甲氧基羰基羟甲基尿苷（mchmUs）及其酸类似物（chmUs）。
First organocatalytic, diastereoselective synthesis of tRNA wobble nucleosides: ()- and ()-methoxycarbonylhydroxymethyluridines (mchmUs) and their acid analogues (chmUs).
作者信息
Bartosik Tomasz, Dziergowska Agnieszka, Kowalski Blazej, Leszczynska Grazyna
机构信息
Lodz University of Technology, Institute of Organic Chemistry Zeromskiego 116 90-924 Lodz Poland
出版信息
RSC Adv. 2025 Jul 29;15(33):26943-26949. doi: 10.1039/d5ra04760a. eCollection 2025 Jul 25.
A diastereoselective organocatalytic synthesis of ()- and ()-methoxycarbonylhydroxymethyluridines (mchmUs) and their acid analogues (chmUs) was developed. The method employs organo- and organometallic-catalyzed cyanosilylation of 5-formyluridine to yield diastereomerically enriched TMS-protected cyanohydrins, which are converted a Pinner reaction to ()- and ()-mchmUs, then hydrolyzed to ()- and ()-chmUs.
开发了一种非对映选择性有机催化合成（）-和（）-甲氧基羰基羟甲基尿苷（mchmUs）及其酸类似物（chmUs）的方法。该方法采用有机和有机金属催化的5-甲酰基尿苷的氰基硅烷化反应，生成非对映体富集的TMS保护的氰醇，通过Pinner反应将其转化为（）-和（）-mchmUs，然后水解得到（）-和（）-chmUs。
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