Synthesis of the first ferrocene-labeled dideoxynucleotide and its use for 3′-redox end-labeling of 5′-modified single-stranded oligonucleotides

被引:47
作者
Anne, A [1 ]
Blanc, B [1 ]
Moiroux, J [1 ]
机构
[1] Univ Paris 07, Electrochim Mol Lab, CNRS, Unite Mixte Rech 7591, F-75251 Paris 05, France
关键词
D O I
10.1021/bc000126l
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
The target ferrocene-labeled dideoxynucleotide compound 5-[N-(beta -ferracenyl-propanoyl)3-amino-propynl-yl] -2',3'-dideoxyuridine 5'-triphosphate, Fc-ddUTP, was synthesized and tested with terminal deoxynucleotidyl transferase for enzymatic S'-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.
引用
收藏
页码:396 / 405
页数:10
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