Reversible diselenide cross-links are formed between oligonucleotides containing 2′-deoxy-6-selenoinosine

TETRAHEDRON LETTERS

卷:59

Article

Liczner, Christopher¹  Grenier, Vincent¹  Wilds, Christopher J.¹ 

[1] Concordia Univ, Dept Chem & Biochem, Montreal, PQ H4B 1R6, Canada

关键词: Chemically modified oligonucleotides;    Selenium;    2 '-Deoxyinosine;    X-ray crystallography;    DNA cross-links;   

DOI  :  10.1016/j.tetlet.2017.11.044

来源: Elsevier

【 摘 要 】

We have synthesized and characterized a phosphoramidite derivative of 2'-deoxy-6-selenoinosine (d(6Se)I) 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 d(6se)I 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. (C) 2017 Elsevier Ltd. All rights reserved.

【 授权许可】

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