Thioctic acid modification of oligonucleotides using an H-phosphonate

Jennifer A. Dougan; Andrew K. Reid; Duncan Graham

doi:10.1016/j.tetlet.2010.08.107

Thioctic acid modification of oligonucleotides using an H-phosphonate

Jennifer A. Dougan, Andrew K. Reid, Duncan Graham

Pure And Applied Chemistry

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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.

Original language	English
Pages (from-to)	5787-5790
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	44
DOIs	https://doi.org/10.1016/j.tetlet.2010.08.107
Publication status	Published - 3 Nov 2010

Keywords

H-phosphonate
thioctic acid
oligonucleotides
phosphoramidite approach
alcohol

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10.1016/j.tetlet.2010.08.107

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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.",

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AU - Reid, Andrew K.

AU - Graham, Duncan

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N2 - 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.

AB - 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.

KW - H-phosphonate

KW - thioctic acid

KW - oligonucleotides

KW - phosphoramidite approach

KW - alcohol

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DO - 10.1016/j.tetlet.2010.08.107

M3 - Article

VL - 51

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EP - 5790

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 44

ER -

Thioctic acid modification of oligonucleotides using an H-phosphonate

Abstract

Keywords

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