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Mutually Orthogonal Bioconjugation of Vinyl Nucleosides for RNA Metabolic Labeling
Organic Letters ( IF 5.2 ) Pub Date : 2021-09-08 , DOI: 10.1021/acs.orglett.1c02584
Mrityunjay Gupta 1 , Monika Singha 2 , Dnyaneshwar B Rasale 2 , Zehao Zhou 3 , Srijana Bhandari 3 , Samantha Beasley 2 , Jasmine Sakr 2 , Shane M Parker 3 , Robert C Spitale 1, 2
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We report a strategy for the orthogonal conjugation of the vinyl nucleosides, 5-vinyluridine (5-VU) and 2-vinyladenosine (2-VA), via selective reactivity with maleimide and tris(2-carboxyethyl)phosphine (TCEP), respectively. The orthogonality was investigated using density functional theory (DFT) and confirmed by reactions with vinyl nucleosides. Further, these chemistries were used to modify RNA for fluorescent cell imaging. These reactions allow for the expanded use of RNA metabolic labeling to study nascent RNA expression within different RNA populations.

中文翻译:

用于 RNA 代谢标记的乙烯基核苷的相互正交生物共轭

我们报告了乙烯基核苷、5-乙烯基尿苷 (5-VU) 和 2-乙烯基腺苷 (2-VA) 的正交共轭策略,分别通过与马来酰亚胺和三 (2-羧乙基) 膦 (TCEP) 的选择性反应。使用密度泛函理论 (DFT) 研究正交性,并通过与乙烯基核苷的反应确认。此外,这些化学物质用于修饰 RNA 以进行荧光细胞成像。这些反应允许扩大使用 RNA 代谢标记来研究不同 RNA 群体中的新生 RNA 表达。
更新日期:2021-09-17
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