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Laboratoire d'Electrochimie Moleculaire, LEM, Paris

UMR CNRS - Université Paris Diderot - Paris France

   
 
Master Frontiers in Chemistry | UFR de Chimie - Université Paris Diderot - Paris 7 CNRS - Institut de chimie Université de Paris Master Chimie Sorbonne Paris Cité UFR de Chimie - Université Paris Diderot - Paris 7 CNRS - Institut de chimie
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Université Paris Diderot
Université de Paris CNRS, Centre National de la Recherche Scientifique
 
 


Le LEM - Publications: Abstracts

Publication 534


Bioconjugate Chem., 12 (3), 396 -405, 2001
DOI: 10.1021/bc000126l S1043-1802(00)00126-9
 

 


Synthesis of the First Ferrocene-Labeled Dideoxynucleotide and Its Use for 3'-Redox End-Labeling of 5'-Modified Single-Stranded Oligonucleotides

Agnès Anne, Bernard Blanc, and Jacques Moiroux

Contribution from the 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


The target ferrocene-labeled dideoxynucleotide compound 5-[N-(-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.

 
   
 
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