Synthesis and biophysical characterization of oligonucleotides containing a 4'-selenonucleotide

Watts, Jonathan K., Johnston, Blair D., Jayakanthan, Kumarasamy, Wahba, Alexander S., Pinto, B. Mario and Damha, Masad J. (2008) Synthesis and biophysical characterization of oligonucleotides containing a 4'-selenonucleotide. Journal of the American Chemical Society, 130 (27), 8578-8579. (doi:10.1021/ja802205u). (PMID:18543920)

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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