Synthesis of the first ferrocene-labeled dideoxynucleotide and its use for 3′-redox end-labeling of 5′-modified single-stranded oligonucleotides
Synthesis of the first ferrocene-labeled dideoxynucleotide and its use for 3′-redox end-labeling of 5′-modified single-stranded oligonucleotides
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DOI：
10.1021/bc000126l
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发表时间：
2001-05-01
影响因子：
4.7
通讯作者：
Moiroux, J
中科院分区：
文献类型：
--
作者：
Anne, A;Blanc, B;Moiroux, J
合成了目标二茂铁标记的双脱氧核苷酸化合物5-[N-（β-二茂铁基-丙酰基）3-氨基-丙炔基]-2 '，3'-双脱氧尿苷5 '-三磷酸（Fc-ddUTP），并用末端脱氧核苷酸转移酶测试了5'-磷酸化单链寡脱氧核苷酸的酶促S '-氧化还原活性末端标记。从容易获得的5-碘尿苷和3-二茂铁基丙酸开始，这里阐述的合成策略遵循温和的多步路线。每个步骤都涉及可靠的方法，并且所有二茂铁中间体都可以轻松纯化。5 '-磷酸化的寡核苷酸的酶促3'-二茂铁末端标记是非常有效的，因此可以制备足够量的3 '-二茂铁标记的寡核苷酸以进一步用于表面修饰。
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.