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在核苷和寡核糖核苷酸水平上,将N-苏氨甲酰腺苷(tA)高效转化为tRNA天然乙内酰脲环化形式(ctA)。

Efficient conversion of N-threonylcarbamoyladenosine (tA) into a tRNA native hydantoin cyclic form (ctA) performed at nucleoside and oligoribonucleotide levels.

作者信息

Matuszewski Michal, Debiec Katarzyna, Sochacka Elzbieta

机构信息

Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland.

出版信息

Chem Commun (Camb). 2017 Jul 11;53(56):7945-7948. doi: 10.1039/c7cc03560h.

Abstract

A tA nucleoside was efficiently and stereospecifically transformed into a hydantoin cyclic form of N-l-threonylcarbamoyladenosine (ctA) by the use of polymer bounded carbodiimide (EDC-P) and HOBt. The procedure was successfully applied for a post-synthetic conversion of tA-containing RNA 17-mers (of the sequences of anticodon stem and loop (ASL) fragments of S. pombe tRNA and E. coli tRNA) into the products bearing the ctA unit.

摘要

通过使用聚合物负载的碳二亚胺(EDC-P)和1-羟基苯并三唑(HOBt),N⁶-反式-对羟基苯甲酰基腺苷(tA)核苷被高效且立体选择性地转化为N¹-苏氨甲酰基腺苷(ctA)的乙内酰脲环化形式。该方法成功应用于含tA的RNA 17聚体(来自粟酒裂殖酵母tRNA和大肠杆菌tRNA的反密码子茎环(ASL)片段序列)的合成后转化,生成带有ctA单元的产物。

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