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- Title
Expanding the Scope of 2'-SCF<sub>3</sub> Modified RNA.
- Authors
Jud, Lukas; Košutić, Marija; Schwarz, Veronika; Hartl, Markus; Kreutz, Christoph; Bister, Klaus; Micura, Ronald
- Abstract
The 2'-trifluoromethylthio (2'-SCF3) modification endows ribonucleic acids with exceptional properties and has attracted considerable interest as a reporter group for NMR spectroscopic applications. However, only modified pyrimidine nucleosides have been generated so far. Here, the syntheses of 2'-SCF3 adenosine and guanosine phosphoramidites of which the latter was obtained in highly efficient manner by an unconventional Boc-protecting group strategy, are reported. RNA solid-phase synthesis provided site-specifically 2'-SCF3-modified oligoribonucleotides that were investigated intensively. Their excellent behavior in 19F NMR spectroscopic probing of RNA ligand binding was exemplified for a noncovalent small molecule-RNA interaction. Moreover, comparably to the 2'-SCF3 pyrimidine nucleosides, the purine counterparts were also found to cause a significant thermodynamic destabilization when located in double helical regions. This property was considered beneficial for siRNA design under the aspect to minimize off-target effects and their performance in silencing of the BASP1 gene was demonstrated.
- Subjects
TRIFLUOROMETHYL compounds; SMALL interfering RNA; NUCLEIC acids spectra; RNA; PYRIMIDINES; NUCLEAR magnetic resonance spectroscopy
- Publication
Chemistry - A European Journal, 2015, Vol 21, Issue 29, p10400
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201500415