Expanding the Scope of 2′‐SCF3 Modified RNA
Year: 2015
Type: article
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 (19) F 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.
Source: Chemistry - A European Journal
Authors: Lukas Jud, Marija Košutić, Veronika Schwarz, Markus Hartl, Christoph Kreutz, Klaus Bister, Ronald Micura
Institution: Universität Innsbruck
Language: English
Subfield: Molecular Biology
Domain: Life Sciences
Open Access status: green
Estimated APC paid: $3,262
Awards: Single-molecule FRET investigations of riboswitch-mediated translational control, Investigating RNA folding and chaperone activity by multidimensional NMR spectroscopy, Resolving excited states of a ribozyme by NMR, """RNPnet"" - RNP structure, function and mechanism of action", Function and Inhibition of Oncogenic Transcription Factors
OpenAlex ID: W2136128420