Fluorinated diaminocyclopentanes as chiral sensitive NMR probes of RNA structure.

Roba Moumné (1, 2) , Morgane Pasco , Elise Prost (3) , Thomas Lecourt (3) , Laurent Micouin (3) , Carine Tisné (4)

1 SSFMB - Synthèse, Structure et Fonction de Molécules Bioactives
2 UPMC - Université Pierre et Marie Curie - Paris 6
3 SSMIP - Synthèse et structure de molécules d'interet pharmacologique
4 LCRB - UMR 8015 - Laboratoire de cristallographie et RMN biologiques

The supramolecular chiral recognition between rac-2a and several structured RNA leads to a distinct (19)F NMR signal splitting. The (19)F NMR analysis of the diastereomeric pairs formed upon binding of this racemic probe delivers a topological footprint of the RNA. This phenomenon can be exploited to investigate dynamic events involving structural equilibria, as demonstrated in a melting experiment. This work provides a proof of concept that small fluorinated moderate binders can act as external probes of RNA structures.

Domaines: Chimie organique

Roba Moumné, Morgane Pasco, Elise Prost, Thomas Lecourt, Laurent Micouin, et al.. Fluorinated diaminocyclopentanes as chiral sensitive NMR probes of RNA structure.. Journal of the American Chemical Society, 2010, 132 (38), pp.13111-3. ⟨10.1021/ja1037885⟩. ⟨hal-00614591⟩