title: A versatile post-synthetic method on a solid support for the synthesis of RNA containing reduction-responsive modifications.
abstract: An original post-synthetic method on a solid support was developed to introduce various disulfide bond containing groups at the 2'-OH of oligoribonucleotides (RNAs). It is based on a thiol disulfide exchange reaction between several readily accessible alkyldisulfanyl-pyridine derivatives and 2'-O-acetylthiomethyl RNA in the presence of butylamine. By this strategy, diverse 2'-O-alkyldithiomethyl RNAs were obtained. These modifications provided high nuclease resistance to RNA and were easily removed with glutathione treatment, thus featuring a potential use for siRNA prodrugs.
authors.affiliation: Department of Nucleic Acids, IBMM, UMR 5247, CNRS, Université de Montpellier, ENSCM, UM Campus Triolet, Place E. Bataillon, 34095 Montpellier Cedex 05, France. christelle.dupouy@umontpellier.fr françoise.debart@umontpellier.fr.
authors.forename: Annabelle
authors.initials: A
authors.lastname: Biscans
authors.forename: Sonia
authors.initials: S
authors.lastname: Rouanet
authors.forename: Jean-Jacques
authors.initials: JJ
authors.lastname: Vasseur
authors.forename: Christelle
authors.initials: C
authors.lastname: Dupouy
authors.forename: Françoise
authors.initials: F
authors.lastname: Debart
mesh_terms: D004220:Disulfides / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011355:Prodrugs / Q000138:chemical synthesis* / Q000737:chemistry; D012313:RNA / Q000737:chemistry*; D034741:RNA, Small Interfering / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004220:Disulfides; D011355:Prodrugs; D034741:RNA, Small Interfering; D012313:RNA