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Nucleic Acids Research 2004 32(17):5310-5319; doi:10.1093/nar/gkh874
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Published online 5 October 2004

Nucleic Acids Research, Vol. 32 No. 17 © Oxford University Press 2004; all rights reserved

Automated synthesis of new ferrocenyl-modified oligonucleotides: study of their properties in solution

Aude-Emmanuelle Navarro, Nicolas Spinelli1, Corinne Moustrou, Carole Chaix1, Bernard Mandrand1 and Hugues Brisset*

Groupe de Chimie Organique Matériaux Moléculaires, UMR CNRS 6114, Faculté des Sciences de Luminy, 163 avenue de Luminy, 13288 Marseille Cedex 9, France and 1 Systèmes Macromoléculaires et Immunovirologie Humaine, UMR CNRS 2714, Ecole Normale Supérieure de Lyon, 46 allée d'Italie, 69007 Lyon, France

* To whom correspondence should be addressed. Tel: +33 4 91 82 95 87; Fax: +33 4 91 82 95 80; Email: brisset{at}luminy.univ-mrs.fr
Correspondence may also be addressed to Carole Chaix. Tel: +33 4 72 72 83 64; Fax: +33 4 72 72 85 33; Email: Carole.Chaix{at}ens-lyon.fr

Received May 11, 2004; Revised July 7, 2004; Accepted September 19, 2004

We have developed new ferrocenyl-modified oligonucleotide (ODN) probes for electrochemical DNA sensors. A monofunctional ferrocene containing phosphoramidite group has been prepared, and a new bisfunctional ferrocene containing phosphoramidite and dimethoxytrityl (DMT) groups has been developed. These ferrocenyl-phosphoramidites have been directly employed in an automated solid-phase DNA synthesizer using phosphoramidite chemistry. The advantages of this method are that it allows a non-specialist in nucleotide chemistry to access labeled ODNs and that it has demonstrated good results. ODNs modified at the 3' and/or 5' extremities have been prepared, with the incorporation of the ferrocenyl group into the chain. The 5' position appears to be more important due to its particular behavior. The thermal stability and electrochemical properties of these new ODN ferrocenes were analyzed before and after hybridization with different ODNs. The feasibility of using these new ferrocenyl-labeled ODNs in DNA sensors has been demonstrated.


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