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Syntheses of 2'-C-amidoalkyl and 2'-C-cyanoalkyl containing oligodeoxyribonucleotides and assessment of their hybridisation affinity for complementary DNA and RNA

Syntheses of 2'-C-amidoalkyl and 2'-C-cyanoalkyl containing oligodeoxyribonucleotides and assessment of their hybridisation affinity for complementary DNA and RNA
Syntheses of 2'-C-amidoalkyl and 2'-C-cyanoalkyl containing oligodeoxyribonucleotides and assessment of their hybridisation affinity for complementary DNA and RNA
Oligodeoxynucleotides containing 2?-C-branched nucleosides with an amide or nitrile appended to either a one or two carbon alkyl chain have been synthesised. The phosphoramidites of the 2?-C-modified nucleosides were prepared and incorporated into the oligonucleotides using automated DNA synthesis. The duplex stability with complementary RNA and DNA was measured by UV melting experiments, in order to assess whether the amide/nitrile function could induce any duplex stability without the presence of the 2?-oxygen. The duplex stabilities of the oligonucleotides containing the 2?-C-modifications were decreased in the absence of the 2?-oxygen.
nucleotide, oligonucleotides, duplex stability, duplexes, analogs, nucleosides, hybrids, stability, antisense, nuclease resistance, 2'-c-modified nucleosides
0040-4020
577-585
Brennan, Lavinia
bbf2c574-d0aa-469f-b7c2-04eac8ee660a
Cosstick, Richard
c863fc03-bcbe-4e09-8896-805aa919afee
O'Neil, Ian A.
fcc0f99f-a8b4-4607-9280-83cf724de1c4
Van Aerschot, Arthur
6946b3af-92cd-4d46-bd75-d3f1fa7f80d5
Brennan, Lavinia
bbf2c574-d0aa-469f-b7c2-04eac8ee660a
Cosstick, Richard
c863fc03-bcbe-4e09-8896-805aa919afee
O'Neil, Ian A.
fcc0f99f-a8b4-4607-9280-83cf724de1c4
Van Aerschot, Arthur
6946b3af-92cd-4d46-bd75-d3f1fa7f80d5

Brennan, Lavinia, Cosstick, Richard, O'Neil, Ian A. and Van Aerschot, Arthur (2007) Syntheses of 2'-C-amidoalkyl and 2'-C-cyanoalkyl containing oligodeoxyribonucleotides and assessment of their hybridisation affinity for complementary DNA and RNA. Tetrahedron, 63 (3), 577-585. (doi:10.1016/j.tet.2006.11.024).

Record type: Article

Abstract

Oligodeoxynucleotides containing 2?-C-branched nucleosides with an amide or nitrile appended to either a one or two carbon alkyl chain have been synthesised. The phosphoramidites of the 2?-C-modified nucleosides were prepared and incorporated into the oligonucleotides using automated DNA synthesis. The duplex stability with complementary RNA and DNA was measured by UV melting experiments, in order to assess whether the amide/nitrile function could induce any duplex stability without the presence of the 2?-oxygen. The duplex stabilities of the oligonucleotides containing the 2?-C-modifications were decreased in the absence of the 2?-oxygen.

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More information

Published date: 15 January 2007
Keywords: nucleotide, oligonucleotides, duplex stability, duplexes, analogs, nucleosides, hybrids, stability, antisense, nuclease resistance, 2'-c-modified nucleosides

Identifiers

Local EPrints ID: 54251
URI: https://eprints.soton.ac.uk/id/eprint/54251
ISSN: 0040-4020
PURE UUID: 4b3ab616-828b-44e2-9326-8c39e805d7b4

Catalogue record

Date deposited: 31 Jul 2008
Last modified: 13 Mar 2019 20:39

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