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A 2′,2′-disulfide-bridged dinucleotide conformationally locks RNA hairpins

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Abstract

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.

Graphical abstract: A 2′,2′-disulfide-bridged dinucleotide conformationally locks RNA hairpins

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Publication details

The article was received on 07 Feb 2018, accepted on 04 Apr 2018 and first published on 05 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00328A
Citation: Org. Biomol. Chem., 2018, Advance Article
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    A 2′,2′-disulfide-bridged dinucleotide conformationally locks RNA hairpins

    F. Gauthier, F. Beltran, A. Biscans, F. Debart, C. Dupouy and J. Vasseur, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00328A

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