Automated synthesis of new ferrocenyl-modified oligonucleotides: study of their properties in solution.
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.
Groupe de Chimie Organique Matériaux Moléculaires, UMR CNRS 6114, Faculté des Sciences de Luminy, 163 avenue de Luminy, 13288 Marseille Cedex 9, France.
Aude-Emmanuelle
AE
Navarro
Nicolas
N
Spinelli
Corinne
C
Moustrou
Carole
C
Chaix
Bernard
B
Mandrand
Hugues
H
Brisset
D015374:Biosensing Techniques / Q000379:methods*; D004247:DNA / Q000032:analysis*; D004563:Electrochemistry; D005296:Ferrous Compounds / Q000737:chemistry*; D000075163:Metallocenes; D009691:Nucleic Acid Denaturation; D009693:Nucleic Acid Hybridization / Q000379:methods*; D015345:Oligonucleotide Probes / Q000138:chemical synthesis / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry*
D005296:Ferrous Compounds; D000075163:Metallocenes; D015345:Oligonucleotide Probes; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D004247:DNA; C004998:ferrocene