Liczner, Christopher, Grenier, Vincent and Wilds, Christopher J. (2017) Reversible Diselenide Cross-links are Formed Between Oligonucleotides Containing 2’-Deoxy-6-selenoinosine. Tetrahedron Letters . ISSN 00404039 (In Press)
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Official URL: http://dx.doi.org/10.1016/j.tetlet.2017.11.044
Abstract
We have synthesized and characterized a phosphoramidite derivative of 2’-deoxy-6-selenoinosine (d6SeI) and incorporated this modification into an oligonucleotide by solid-phase synthesis. During cleavage from the solid-support and deprotection, spontaneous dimerization of this oligonucleotide occurs via formation of a diselenide cross-link between the modified nucleobases. This cross-link can be readily reduced to restore the single-stranded oligonucleotide. UV thermal denaturation and circular dichroism spectroscopy of duplexes with d6SeI paired against all four native nucleobases revealed minor differences in stability and structure relative to 2’-deoxyinosine. This selenium containing nucleobase modification may be useful for applications in DNA nanomaterials and X-ray crystallography.
| Divisions: | Concordia University > Faculty of Arts and Science > Chemistry and Biochemistry |
|---|---|
| Item Type: | Article |
| Refereed: | Yes |
| Authors: | Liczner, Christopher and Grenier, Vincent and Wilds, Christopher J. |
| Journal or Publication: | Tetrahedron Letters |
| Date: | 21 November 2017 |
| Funders: |
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| Digital Object Identifier (DOI): | 10.1016/j.tetlet.2017.11.044 |
| Keywords: | Chemically modified oligonucleotides; Selenium; 2’-deoxyinosine; X-ray crystallography; DNA cross-links |
| ID Code: | 983223 |
| Deposited By: | Danielle Dennie |
| Deposited On: | 22 Nov 2017 19:16 |
| Last Modified: | 20 Nov 2018 01:00 |
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