Thioctic acid modification of oligonucleotides using an H-phosphonate

Dougan, Jennifer A. and Reid, Andrew K. and Graham, Duncan (2010) Thioctic acid modification of oligonucleotides using an H-phosphonate. Tetrahedron Letters, 51 (44). pp. 5787-5790. ISSN 0040-4039

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Abstract

The H-phosphonate of a derivative of thioctic acid (TA) was synthesized and used to introduce a disulfide moiety at the 5'-end of oligonucleotides. This method overcomes the difficulties experienced with the phosphoramidite approach when employing a cyclic disulfide in the starting alcohol. The disulfide-modified oligonucleotides are subsequently used in metallic nanoparticle (Au and Ag) and surface functionalisation for sensitive, sequence specific analytical detection strategies.