Issue 23, 2005
From the journal:

Organic & Biomolecular Chemistry

Stabilization of tandem dG–dA base pairs in DNA-hairpins: replacement of the canonical bases by 7-deaza-7-propynylpurines†

Frank Seela,*ab   Simone Budow,ab   Khalil I. Shaikhab  and  Anup M. Jawalekarab  

* Corresponding authors

a Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastraße 7, 49069 Osnabrück, Germany

b Center for Nanotechnology, Gievenbecker Weg 11, 48149 Münster, Germany
E-mail: Frank.Seela@uni-osnabrueck.de;
Web: http://www.seela.net
Fax: +49-541-9692370
Tel: +49-541-9692791

Abstract

The stabilizing effect of 7-propynylated 7-deazapurine nucleosides on DNA-hairpins and DNA-duplexes containing d(GA) mismatches was investigated. The corresponding oligonucleotides were synthesized using solid-phase synthesis. For this purpose, the phosphoramidite of 7-deaza-7-propynyl-2′-deoxyadenosine (3c) was prepared. The incorporation of 3c instead of dA into the tandem d(GA) base pair of a DNA-hairpin alters the secondary structure, but has a positive effect on the duplex stability. A complete replacement of the canonical nucleosides of the tandem d(GA) base pair by 3c and 7-deaza-7-propynyl-2′-deoxyguanosine results in a significant base pair stabilization.

Graphical abstract: Stabilization of tandem dG–dA base pairs in DNA-hairpins: replacement of the canonical bases by 7-deaza-7-propynylpurines

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Article information

DOI
https://doi.org/10.1039/B510444K
Article type
Paper
Submitted
22 Jul 2005
Accepted
23 Sep 2005
First published
20 Oct 2005

Org. Biomol. Chem., 2005,3, 4221-4226

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Stabilization of tandem dG–dA base pairs in DNA-hairpins: replacement of the canonical bases by 7-deaza-7-propynylpurines

F. Seela, S. Budow, K. I. Shaikh and A. M. Jawalekar, Org. Biomol. Chem., 2005, 3, 4221 DOI: 10.1039/B510444K

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