A 2′,2′-disulfide-bridged dinucleotide conformationally locks RNA hairpinsElectronic supplementary information (ESI) available: Synthesis of cytidine, adenosine and guanosine phosphoramidite 1a-c and modified sequences, NMR spectra of intermediate and phosphoramidite 1a-c, analytical data of 2′-O-disulfide-bridged RNA sequences, Tm data and CD spectra of ONs, gel electrophoresis with SVPDE, fluorescence emission spectra with labelled ONs. See DOI: 10.1039/c8ob00328a

The synthesis and the impact of a disulfide bridge between 2′- O -positions of two adjacent nucleotides in an RNA duplex and in the loop of RNA hairpins are reported. The incorporation of this 2′,2′-disulfide (S-S) bridge enabled thermal and enzymatic stabilization of the hairpin depending on its po...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Hauptverfasser: Gauthier, Florian, Beltran, Frédéric, Biscans, Annabelle, Debart, Françoise, Dupouy, Christelle, Vasseur, Jean-Jacques
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The synthesis and the impact of a disulfide bridge between 2′- O -positions of two adjacent nucleotides in an RNA duplex and in the loop of RNA hairpins are reported. The incorporation of this 2′,2′-disulfide (S-S) bridge enabled thermal and enzymatic stabilization of the hairpin depending on its position in the loop. The influence of the disulfide bridge on RNA folding was studied at the HIV Dimerization Initiation Site (DIS) as an RNA sequence model. We have shown that this S-S bridge locked the hairpin form, whereas the extended duplex form was generated after the reduction of the disulfide bond in the presence of tris(2-carboxyethyl)phosphine or glutathione. Thus, the S-S bridge can be useful for understanding RNA folding; an RNA molecular beacon locked by an S-S bridge was also investigated as a sensor for the detection of glutathione. We report the effect of a 2′,2′-disulfide bridge in the loop of the RNA hairpins and its application as a molecular beacon.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob00328a