Synthesis of the first ferrocene-labeled dideoxynucleotide and its use for 3'-redox end-labeling of 5'-modified single-stranded oligonucleotides.
The target ferrocene-labeled dideoxynucleotide compound 5-[N-(beta-ferrocenyl-propanoyl)3-amino-propyn-1-yl]-2',3'-dideoxyuridine 5'-triphosphate, Fc-ddUTP, was synthesized and tested with terminal deoxynucleotidyl transferase for enzymatic 3'-redox-active end-labeling of 5'-phosphorylated single-stranded oligodeoxynucleotides. Starting from readily available 5-iodouridine and 3-ferrocenylpropanoic acid, the synthetic strategy elaborated here follows a mild multistep route. Each step involves reliable methods, and all ferrocene intermediates can be easily purified. Enzymatic 3'-ferrocene end-labeling of 5'-phosphorylated oligonucleotides is remarkably efficient, and 3'-ferrocene-labeled oligonucleotides can thus be prepared in sufficient amounts for further use in surface modifications.
Anne
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A
Laboratoire d'Electrochimie Moléculaire, Unité Mixte de Recherche Université-CNRS No 7591, Université de Paris 7 - Denis Diderot, 2 place Jussieu, 75251 Paris Cedex 05, France. anne@paris7.jussieu.fr
Blanc
B
B
Moiroux
J
J
D000818:Animals; D004253:DNA Nucleotidylexotransferase / Q000378:metabolism; D015342:DNA Probes / Q000138:chemical synthesis*; D003856:Deoxyuracil Nucleotides; D003857:Deoxyuridine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D054306:Dideoxynucleotides; D005296:Ferrous Compounds / Q000138:chemical synthesis; D006801:Humans; D000075163:Metallocenes; D009841:Oligonucleotides / Q000378:metabolism*; D010084:Oxidation-Reduction; D014500:Uracil Nucleotides / Q000138:chemical synthesis
C438936:5-(N-(beta-ferrocenyl-propanoyl)3-amino-propyn-1-yl)-2',3'-dideoxyuridine 5'-triphosphate; D015342:DNA Probes; D003856:Deoxyuracil Nucleotides; D054306:Dideoxynucleotides; D005296:Ferrous Compounds; D000075163:Metallocenes; D009841:Oligonucleotides; D014500:Uracil Nucleotides; C063034:2',3'-dideoxyuridine-5'-triphosphate; D004253:DNA Nucleotidylexotransferase; C004998:ferrocene; D003857:Deoxyuridine