使用三聚磷酸从2'-3'-保护的核苷合成三磷酸核苷。
Synthesis of Nucleoside Triphosphates from 2'-3'-Protected Nucleosides Using Trimetaphosphate.
作者信息
Mohamady Samy, Taylor Scott D
机构信息
Faculty of Pharmacy, The British University in Egypt , Cairo-Suez Desert Road, 11837 Cairo, Egypt.
Department of Chemistry, University of Waterloo , 200 University Avenue West, Waterloo, Ontario, Canada N2L 3G1.
出版信息
Org Lett. 2016 Feb 5;18(3):580-3. doi: 10.1021/acs.orglett.5b03624. Epub 2016 Jan 13.
Chemists have been attempting to triphosphorylate nucleosides and other alcohols using trimetaphosphate (TriMP) since the 1960s. However, this route appears to have been abandoned due to poor yields. The first practical syntheses of nucleoside triphosphates (NTPs) are reported using TriMP as the key reagent. This was achieved by reacting the tetrabutylammonium salt of TriMP with mesitylenesulfonyl chloride in the presence of DABCO in pyridine followed by the addition of an appropriately protected nucleoside and phthalimide. Quenching the reaction with aqueous buffer followed by hydrolysis of the OH protecting groups gave the NTPs in good yield.
自20世纪60年代以来，化学家们一直试图用偏三磷酸（TriMP）将核苷和其他醇类进行三磷酸化。然而，由于产率低，这条路线似乎已被放弃。据报道，首次以TriMP作为关键试剂实现了核苷三磷酸（NTP）的实际合成。这是通过使TriMP的四丁铵盐与均三甲苯磺酰氯在吡啶中于DABCO存在下反应，然后加入适当保护的核苷和邻苯二甲酰亚胺来实现的。用水性缓冲液淬灭反应，随后水解OH保护基团，以良好的产率得到NTP。
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