Innately Water-Soluble Isatoic Anhydrides with Modulated Reactivities for RNA SHAPE Analysis.,Bioconjugate Chemistry

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Innately Water-Soluble Isatoic Anhydrides with Modulated Reactivities for RNA SHAPE Analysis.
Bioconjugate Chemistry ( IF 4.0 ) Pub Date : 2020-02-17 , DOI: 10.1021/acs.bioconjchem.0c00024
Adam B Fessler , Abhishek Dey , Dominic S Finis , Anthony J Fowler ₁ , Kausik Chakrabarti , Craig A Ogle

Affiliation

1-Methyl-7-nitroisatoic anhydride (1M7) and 2-methylnicotinic acid imidazolide (NAI) are two of the most commonly applied RNA-SHAPE electrophiles; 1M7 due to its high reactivity and NAI for its solubility and cell permeability. While the addition of a nitro group yields desirable activation of the reagent, it also leads to poorer water solubility. This limited solubility has motivated the development of water-soluble reagents. We present alternative, isatoic anhydride-based reagents possessing variable reactivities that are simultaneously water-soluble. Solubility is gained by using a quaternary ammonium, while modulation of the reactivity is obtained by functionalization of the aryl ring. The syntheses of the reagents are discussed, and the electrophiles are demonstrated to be suitable for use for an in vitro RNA SHAPE experiment when directly compared to 1M7.

中文翻译：

具有固有的水溶性等规酸酐，具有可调节的RNA形状分析反应性。

1-甲基-7-亚硝基尿酸酐（1M7）和2-甲基烟酰胺基咪唑啉（NAI）是两种最常用的RNA-SHAPE亲电试剂。1M7具有高反应活性，NAI具有较高的溶解度和细胞渗透性。尽管添加硝基产生期望的试剂活化，但是它也导致较差的水溶性。这种有限的溶解度促进了水溶性试剂的开发。我们提出了具有可变反应性且同时可溶于水的替代品，基于等酸酐的试剂。通过使用季铵获得溶解性，而通过芳基环的官能化获得反应性的调节。讨论了试剂的合成，

更新日期：2020-02-17

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