Adam B. Fessler, A. Dey, Dominic S Finis
Feb 10, 2020
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Influential Citations
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Journal
Bioconjugate chemistry
Abstract
1-methyl-7-nitroisatoic anhydride (1M7) and 2-methylnicotinic acid imidazolide (NAI) are two of the most com-monly 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 syn-theses 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.