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3'-硫代酰胺修饰的3'-脱氧胸苷-5'-三磷酸酯的合成及其在桑格DNA测序中作为链终止剂的应用。

Synthesis of 3'-thioamido-modified 3'-deoxythymidine-5'-triphosphates and their use as chain terminators in Sanger-DNA sequencing.

作者信息

Schwarzer K, Wojczewski C, Engels J W

机构信息

Johann Wolfgang Goethe-Universität, Frankfurt am Main, Germany.

出版信息

Nucleosides Nucleotides Nucleic Acids. 2001 Apr-Jul;20(4-7):879-82. doi: 10.1081/NCN-100002450.

DOI:10.1081/NCN-100002450
PMID:11563136
Abstract

The thioamide derivatives 3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-[(2-methyl-1-thioxo- propyl)amino]thymidine 1 and 3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-((6-([(9H-(fluo-ren-9- ylmethoxy)carbonyl]-amino)-1-thioxohexyl)amino) thymidine 2 were synthesized by regioselective thionation of their corresponding amides 7 and 8 with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (Lawesson's reagent). The thioamides were converted into the corresponding 5'-triphosphates 3 and 4. Compound 3 was chosen for DNA sequencing experiments and 4 was further labelled with fluorescein.

摘要

硫代酰胺衍生物3'-脱氧-5'-O-(4,4'-二甲氧基三苯甲基)-3'-[(2-甲基-1-硫代丙基)氨基]胸苷1和3'-脱氧-5'-O-(4,4'-二甲氧基三苯甲基)-3'-((6-([(9H-芴-9-基甲氧基)羰基]-氨基)-1-硫代己基)氨基)胸苷2是通过用2,4-双(4-甲氧基苯基)-1,3,2,4-二硫代二磷杂环丁烷-2,4-二硫化物(劳森试剂)对其相应的酰胺7和8进行区域选择性硫代反应合成的。硫代酰胺被转化为相应的5'-三磷酸酯3和4。选择化合物3进行DNA测序实验,化合物4进一步用荧光素标记。

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