Thioctic acid modification of oligonucleotides using an H-phosphonate

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

Research output: Contribution to journal › Article

5 Citations (Scopus)

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.
LanguageEnglish
Pages5787-5790
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number44
DOIs
Publication statusPublished - 3 Nov 2010

Fingerprint

Thioctic Acid
Organophosphonates
Oligonucleotides
Disulfides
Metal Nanoparticles
Alcohols
Nanoparticles
Derivatives

Keywords

  • H-phosphonate
  • thioctic acid
  • oligonucleotides
  • phosphoramidite approach
  • alcohol

Cite this

Dougan, Jennifer A. ; Reid, Andrew K. ; Graham, Duncan. / Thioctic acid modification of oligonucleotides using an H-phosphonate. In: Tetrahedron Letters. 2010 ; Vol. 51, No. 44. pp. 5787-5790.
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Dougan, JA, Reid, AK & Graham, D 2010, 'Thioctic acid modification of oligonucleotides using an H-phosphonate' Tetrahedron Letters, vol. 51, no. 44, pp. 5787-5790. https://doi.org/10.1016/j.tetlet.2010.08.107

Thioctic acid modification of oligonucleotides using an H-phosphonate. / Dougan, Jennifer A.; Reid, Andrew K.; Graham, Duncan.

In: Tetrahedron Letters, Vol. 51, No. 44, 03.11.2010, p. 5787-5790.

Research output: Contribution to journal › Article

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T1 - Thioctic acid modification of oligonucleotides using an H-phosphonate

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AU - Graham, Duncan

PY - 2010/11/3

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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.

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Dougan JA, Reid AK, Graham D. Thioctic acid modification of oligonucleotides using an H-phosphonate. Tetrahedron Letters. 2010 Nov 3;51(44):5787-5790. https://doi.org/10.1016/j.tetlet.2010.08.107

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