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.
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