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RNA SHAPE chemistry with aromatic acylating reagents.

Nodin L., Noël O., Chaminade F., Maskri O., Barbier V., David O., Fosse P., Xie J. Bioorg Med Chem Lett. 2015 Feb 1;25(3):566-70. doi: 10.1016/j.bmcl.2014.12.020. Dec 15.

As chemical methods for RNA secondary structure determination, SHAPE chemistry (selective 2-hydroxyl acylation analyzed by primer extension) has been developed to specifically target flexible nucleotides (often unpaired nucleotides) independently to their purine or pyrimidine nature. In order to
improve the specificity of acylating reagents towards unpaired nucleotides, we have explored the reactivity of symmetric anhydrides, acyl fluorides, active esters like succinimidyl ester and cyanomethyl esters for 2-O-acylation reaction. Among the tested compounds, only the acyl fluoride 4 showed
a low reactivity (compared to NMIA). However, this study is the first to show that nucleophilic catalysts like DMAP greatly improved the selective 2-hydroxyl acylation by symmetric anhydrides, acyl fluorides and succinimidyl ester, with the 2-fluorobenzoic anhydride 5 being the most reactive.