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2?-aminoethoxy-2-amino-3-methylpyridine in triplex-forming oligonucleotides: high affinity, selectivity and resistance to enzymatic degradation

2?-aminoethoxy-2-amino-3-methylpyridine in triplex-forming oligonucleotides: high affinity, selectivity and resistance to enzymatic degradation
2?-aminoethoxy-2-amino-3-methylpyridine in triplex-forming oligonucleotides: high affinity, selectivity and resistance to enzymatic degradation
The phosphoramidite monomer of the C-nucleoside 2?-aminoethoxy-2-amino-3-methylpyridine (AE-MAP) has been synthesized for the first time and incorporated into triplex-forming oligonucleotides (TFOs). Ultraviolet melting and DNase I footprinting studies show that AE-MAP is a potent triplex-stabilizing monomer that is selective for GC base pairs. TFOs containing AE-MAP bind with high affinity to duplexes but only weakly to single stranded DNA. In addition, AE-MAP confers high nuclease resistance on oligonucleotides. TFOs containing AE-MAP have potential for gene knock-out and gene expression studies.

0947-6539
14851-14856
Lou, Chenguang
bf8d79e9-a81a-4483-ab89-13244aac3eb6
Shelbourne, Montserrat
6b004f69-8f1e-4b4d-a8a3-f7dc3f149639
Fox, Keith R.
9da5debc-4e45-473e-ab8c-550d1104659f
Brown, Tom
1cd7df32-b945-4ca1-8b59-a51a30191472
Lou, Chenguang
bf8d79e9-a81a-4483-ab89-13244aac3eb6
Shelbourne, Montserrat
6b004f69-8f1e-4b4d-a8a3-f7dc3f149639
Fox, Keith R.
9da5debc-4e45-473e-ab8c-550d1104659f
Brown, Tom
1cd7df32-b945-4ca1-8b59-a51a30191472

Lou, Chenguang, Shelbourne, Montserrat, Fox, Keith R. and Brown, Tom (2011) 2?-aminoethoxy-2-amino-3-methylpyridine in triplex-forming oligonucleotides: high affinity, selectivity and resistance to enzymatic degradation. Chemistry - A European Journal, 17 (52), 14851-14856. (doi:10.1002/chem.201102287).

Record type: Article

Abstract

The phosphoramidite monomer of the C-nucleoside 2?-aminoethoxy-2-amino-3-methylpyridine (AE-MAP) has been synthesized for the first time and incorporated into triplex-forming oligonucleotides (TFOs). Ultraviolet melting and DNase I footprinting studies show that AE-MAP is a potent triplex-stabilizing monomer that is selective for GC base pairs. TFOs containing AE-MAP bind with high affinity to duplexes but only weakly to single stranded DNA. In addition, AE-MAP confers high nuclease resistance on oligonucleotides. TFOs containing AE-MAP have potential for gene knock-out and gene expression studies.

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Published date: 2011
Related URLs:
Organisations: Molecular and Cellular

Identifiers

Local EPrints ID: 206549
URI: http://eprints.soton.ac.uk/id/eprint/206549
DOI: doi:10.1002/chem.201102287
ISSN: 0947-6539
PURE UUID: 32e6f71e-ae60-4f1c-aa2e-f689349dba33
ORCID for Keith R. Fox: ORCID iD orcid.org/0000-0002-2925-7315

Catalogue record

Date deposited: 22 Dec 2011 16:32
Last modified: 15 Mar 2024 02:36

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Contributors

Author: Chenguang Lou
Author: Montserrat Shelbourne
Author: Keith R. Fox ORCID iD
Author: Tom Brown

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