AN IMPROVED PROTECTION-FREE ONE-POT CHEMICAL SYNTHESIS OF 2′-DEOXYNUCLEOSIDE-5′-TRIPHOSPHATES

AN IMPROVED PROTECTION-FREE ONE-POT CHEMICAL SYNTHESIS OF 2′-DEOXYNUCLEOSIDE-5′-TRIPHOSPHATES
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DOI:
10.1080/15257770.2012.670739
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发表时间:
2012-01-01
影响因子:
1.3
通讯作者:
Srinivasan, Balasubramanian
Srinivasan, Balasubramanian
中科院分区:
生物学4区
文献类型:
--
作者:
Kore, Anilkumar R.;Shanmugasundaram, Muthian;Srinivasan, Balasubramanian

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一种简便、直接、可靠和有效的方法,用于嘌呤脱氧核苷酸如2 ′-脱氧鸟苷-5 ′-三磷酸(dGTP)和2 ′-脱氧腺苷-5 ′-三磷酸(dATP)和嘧啶脱氧核苷酸如2 ′-脱氧胞苷-5 ′-三磷酸(dCTP)、胸苷-5 ′-三磷酸(TTP)的克级化学合成,和2 ′-脱氧尿苷-5 ′-三磷酸(dUTP)。这种改进的“一锅三步”Ludwig合成策略包括核苷的单磷酸化,然后与焦磷酸三丁基铵反应,并水解所得环状中间体,以良好的产率(65%-70%)提供相应的dNTP。
A facile, straightforward, reliable, and an efficient method for the gram-scale chemical synthesis of both purine deoxynucleotides such as 2'-deoxyguanosine-5'-triphosphate (dGTP) and 2'-deoxyadenosine-5'-triphosphate (dATP) and pyrimidine deoxynucleotides such as 2'-deoxycytidine-5'-triphosphate (dCTP), thymidine-5'-triphosphate (TTP), and 2'-deoxyuridine-5'-triphosphate (dUTP) starting from the corresponding nucleoside is described. This improved "one-pot, three step" Ludwig synthetic strategy involves the monophosphorylation of nucleoside followed by reaction with tributylammonium pyrophosphate and hydrolysis of the resulting cyclic intermediate to provide the corresponding dNTP in good yields (65%-70%).