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Reversible Diselenide Cross-links are Formed Between Oligonucleotides Containing 2’-Deoxy-6-selenoinosine


Reversible Diselenide Cross-links are Formed Between Oligonucleotides Containing 2’-Deoxy-6-selenoinosine

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


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
Authors:Liczner, Christopher and Grenier, Vincent and Wilds, Christopher J.
Journal or Publication:Tetrahedron Letters
Date:21 November 2017
  • Natural Sciences and Engineering Research Council of Canada (NSERC, Grants 299384-2011 and RGPIN-2017-06683 to C.J.W.)
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 On:22 Nov 2017 19:16
Last Modified:20 Nov 2018 01:00


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