Synthesis and biophysical characterization of oligonucleotides containing a 4'-selenonucleotide |
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Authors: | Watts Jonathan K Johnston Blair D Jayakanthan Kumarasamy Wahba Alexander S Pinto B Mario Damha Masad J |
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Institution: | Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC, Canada. |
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Abstract: | The first synthesis of oligonucleotides containing 4'-selenium-modified ribonucleotides (4'-Se-rN) is described. Four sequences containing 4'-Se-rT were successfully synthesized and compared with DNA and RNA oligonucleotides containing a dT, rT, or LNA insert in place of the 4'-Se-rT. The 4'-Se-rT behaved more like rT than dT in its effects on binding affinity, despite the DNA-like structure previously observed for the nucleoside, suggesting that a conformational switch occurs upon incorporation into an oligonucleotide. Incorporation of 4'-Se-rT into A-RNA and hybrid duplexes led to increased binding affinity, while incorporation into B-DNA destabilized the duplex to the same extent as an rT nucleotide. |
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