Issue 22, 2010
From the journal:

Organic & Biomolecular Chemistry

CG base pair recognition within DNA triple helices by modified N-methylpyrrolo-dC nucleosides†

Simon R. Gerrard,a   Mastoura M. Edrees,a   Imenne Bouamaied,b   Keith R. Foxc  and  Tom Brown*a  

* Corresponding authors

a School of Chemistry, University of Southampton, Highfield, Southampton, UK.
E-mail: tb2@soton.ac.uk

b ATDBio Ltd, School of Chemistry, University of Southampton, Highfield, Southampton, UK

c School of Biological Sciences, University of Southampton, Bassett Crescent East, Southampton, UK

Abstract

3-Aminophenyl-modified analogues of the bicyclic nucleoside N-methyl-3H-pyrrolo[2,3-d]pyrimidin-2(7H)-one were synthesised and incorporated directly into triplex-forming oligonucleotides in order to utilise their extended hydrogen bonding motif for recognition of the CG base pair. All analogues demonstrated strong binding affinity and very good selectivity for CG from pH 6.2 to 7.0; a marked improvement on previous modifications.

Graphical abstract: CG base pair recognition within DNA triple helices by modified N-methylpyrrolo-dC nucleosides

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Article information

DOI
https://doi.org/10.1039/C0OB00119H
Article type
Paper
Submitted
13 May 2010
Accepted
19 Jul 2010
First published
06 Sep 2010

Org. Biomol. Chem., 2010,8, 5087-5096

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CG base pair recognition within DNA triple helices by modified N-methylpyrrolo-dC nucleosides

S. R. Gerrard, M. M. Edrees, I. Bouamaied, K. R. Fox and T. Brown, Org. Biomol. Chem., 2010, 8, 5087 DOI: 10.1039/C0OB00119H

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