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

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

44 Downloads (Pure)

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

Access to Document

10.1016/j.tetlet.2010.08.107

Link to publication in Scopus

Fingerprint Dive into the research topics of 'Thioctic acid modification of oligonucleotides using an H-phosphonate'. Together they form a unique fingerprint.

Cite this

@article{e73663b7226349a2a4239d22ad1f4e7c,

title = "Thioctic acid modification of oligonucleotides using an H-phosphonate",

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.",

keywords = "H-phosphonate, thioctic acid, oligonucleotides, phosphoramidite approach, alcohol",

author = "Dougan, {Jennifer A.} and Reid, {Andrew K.} and Duncan Graham",

year = "2010",

month = nov,

day = "3",

doi = "10.1016/j.tetlet.2010.08.107",

language = "English",

volume = "51",

pages = "5787--5790",

journal = "Tetrahedron Letters",

issn = "0040-4039",

number = "44",

}

TY - JOUR

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

AU - Dougan, Jennifer A.

AU - Reid, Andrew K.

AU - Graham, Duncan

PY - 2010/11/3

Y1 - 2010/11/3

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

UR - http://www.scopus.com/inward/record.url?scp=77957577049&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2010.08.107

DO - 10.1016/j.tetlet.2010.08.107

M3 - Article

VL - 51

SP - 5787

EP - 5790

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 44

ER -