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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Hartl, Markus Kreutz, Christoph Bister, Klaus Kosutic, Marija Jud, Lukas Schwarz, Veronika Micura, Ronald |
| Description | Author Affiliation: Jud L ( Institute of Organic Chemistry, Center for Molecular Biosciences Innsbruck (CMBI), University of Innsbruck, Innrain 80-82, 6020 Innsbruck (Austria).); Kosutic M ( Institute of Organic Chemistry, Center for Molecular Biosciences Innsbruck (CMBI), University of Innsbruck, Innrain 80-82, 6020 Innsbruck (Austria).); Schwarz V ( Institute of Organic Chemistry, Center for Molecular Biosciences Innsbruck (CMBI), University of Innsbruck, Innrain 80-82, 6020 Innsbruck (Austria).); Hartl M ( Institute of Biochemistry, Center for Molecular Biosciences Innsbruck (CMBI), University of Innsbruck, Innrain 80-82, 6020 Innsbruck (Austria).); Kreutz C ( Institute of Organic Chemistry, Center for Molecular Biosciences Innsbruck (CMBI), University of Innsbruck, Innrain 80-82, 6020 Innsbruck (Austria).); Bister K ( Institute of Biochemistry, Center for Molecular Biosciences Innsbruck (CMBI), University of Innsbruck, Innrain 80-82, 6020 Innsbruck (Austria).); Micura R ( Institute of Organic Chemistry, Center for Molecular Biosciences Innsbruck (CMBI), University of Innsbruck, Innrain 80-82, 6020 Innsbruck (Austria). ronald.micura@uibk.ac.at.) |
| Abstract | The 2′-trifluoromethylthio $(2′-SCF_{3})$ 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 $2′-SCF_{3}$ 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 $2′-SCF_{3}-modified$ 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 $2′-SCF_{3}$ 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. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 29 |
| Volume Number | 21 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2015-07-13 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Fluorine Chemistry Oligonucleotides Organophosphorus Compounds Purines RNA, Small Interfering Crystallography, X-Ray Ligands Magnetic Resonance Spectroscopy Metabolism Solid-Phase Synthesis Techniques Thermodynamics Research Support, Non-U.S. Gov't |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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