Fluorous-Assisted Synthesis of (E)-5-[3-Aminoallyl]-Uridine-5′-O-Triphosphate

Q4 Chemistry
Anilkumar R. Kore, Bo Yang, Balasubramanian Srinivasan
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引用次数: 0

Abstract

An efficient, reliable method for the chemical synthesis of (E)-5-[3-aminoallyl]-uridine-5′-O-triphosphate (AA-UTP), starting from 5-iodouridine, is described. This new strategy features the involvement of one-pot triphosphate formation and fluorous solid-phase extraction (F-SPE). The one-pot synthesis involves the mono phosphorylation of fluorous-tagged uridine, followed by the reaction with pyrophosphate to afford the fluorous-tagged AA-UTP. The F-SPE is achieved by installing a fluorous-tag onto the uridine prior to triphosphate formation, purification via F-SPE, and cleavage of the fluorous-tag. It is worth mentioning that this protocol produces AA-UTP in high yield and purity using one simple F-SPE; no conventional column chromatography is involved. © 2015 by John Wiley & Sons, Inc.

氟辅助合成(E)-5-[3-氨基烯丙基]-尿苷-5 ' - o -三磷酸
介绍了以5-碘吡啶为起始原料,化学合成(E)-5-[3-氨基烯丙基]-尿嘧啶-5′- o -三磷酸(AA-UTP)的一种高效、可靠的方法。这种新策略的特点是涉及一锅三磷酸盐形成和氟固相萃取(F-SPE)。一锅合成包括氟标记尿苷的单磷酸化,然后与焦磷酸反应得到氟标记的AA-UTP。F-SPE是通过在三磷酸形成之前在尿嘧啶上安装一个含氟标签,通过F-SPE纯化,并切割含氟标签来实现的。值得一提的是,该方案采用一个简单的F-SPE,以高收率和纯度生产AA-UTP;不涉及常规柱层析。©2015 by John Wiley &儿子,Inc。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
Current Protocols in Nucleic Acid Chemistry
Current Protocols in Nucleic Acid Chemistry Chemistry-Organic Chemistry
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期刊介绍: Published in association with International Society for Nucleosides, Nucleotides & Nucleic Acids (IS3NA) , Current Protocols in Nucleic Acid Chemistry is equally valuable for biotech, pharmaceutical, and academic labs. It is the resource for designing and running successful research projects in the rapidly growing and changing field of nucleic acid, nucleotide, and nucleoside research.
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