Accès direct au contenu

ENS Cachan - Institut d'Alembert

Version anglaise


Recherche - Valorisation

Identification of acylation products in SHAPE Chemistry

Lin, C., Poyer, S., Zargarian, L., Salpin, J. Y., Fossé, P., Mauffret, O., & Xie, J. (2017). Bioorganic & Medicinal Chemistry Letters.

SHAPE chemistry (selective 2'-hydroxyl acylation analyzed by primer extension) has been developed to specifically target flexible nucleotides for RNA secondary structure determination. However, the structure of 2'-O-acylation products has never been confirmed by NMR or X-ray data. We have realized the acylation reactions between cNMP and NMIA under SHAPE chemistry conditions and identified the acylation products using NMR spectroscopy and mass experiments. For cAMP and cGMP, the major acylation product is the 2'-O-acylated compound (> 99 %). A trace amount of N-acylated cAMP has also been identified by LC-UV-MS². While for cCMP, the isolated acylation products are composed of 96 % of 2'-O-acylated, 4 % of N,O-diacylated, and trace amount of N-acylated products. This interesting result should be useful to explain some unexpected reactivity of the SHAPE chemistry.