Synthesis of nucleoside 5'-O-(1,3-dithiotriphosphates) and 5'-O-(1,1-dithiotriphosphates)
Synthesis of nucleoside 5'-O-(1,3-dithiotriphosphates) and 5'-O-(1,1-dithiotriphosphates)
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核苷 5-O-(1,3-二硫代三磷酸) 和 5-O-(1,1-二硫代三磷酸) 的合成
DOI：
10.1021/jo00005a023
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发表时间：
1991
影响因子：
3.6
通讯作者：
F. Eckstein
中科院分区：
文献类型：
--
作者：
J. Ludwig;F. Eckstein
2-氯- 4h -1,3,2-苯二氮磷-4- 1将3'-脱氧-3'-叠氮胸嘧啶的5'-羟基磷酸化，形成中间体1。1与硫代磷(9)和硫反应生成3'-脱氧-3'-叠氮胸苷5'- o -（1,3-二硫代三磷酸）(5)和3'-脱氧-3'-叠氮胸苷5'- o -（1,2-二硫代三磷酸）(3)的不可分离混合物。另一种生成核苷5′- o -（1,3-二硫代三磷酸）的途径是将核苷5′- o -（1-硫代三磷酸）与Li 2 s反应。当在吡啶/二恶烷中进行该反应时，会生成核苷5′- o -（1,3-二硫代三磷酸）和核苷5′- o -（1,1-二硫代三磷酸）的混合物。后者是在DMF中进行反应时唯一的核苷酸产物
2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one phosphitylates the 5'-hydroxy group of 3'-deoxy-3'-azidothymidine to form intermediate 1. Reaction of 1 with thiopyrophosphate (9) and sulfur results in the formation of an unseparable mixture of 3'-deoxy-3'-azidothymidine 5'-O-(1,3-dithiotriphosphate) (5) and 3'-deoxy-3'-azidothymidine 5'-O-(1,2-dithiotriphosphate) (3). An alternative route to nucleoside 5'-O-(1,3-dithiotriphosphates) consists of reacting a nucleoside 5'-O-(1-thiocyclotriphosphate) with Li 2 S. This reaction, when performed in pyridine/dioxane, leads to a mixture of the nucleoside 5'-O-(1,3-dithiotriphosphate) and the nucleoside 5'-O-(1,1-dithiotriphosphate). The latter is the only nucleotide product when the reaction is carried out in DMF