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在甲酰胺中利用硼酸盐对腺苷进行非生物区域选择性磷酸化。

Abiotic regioselective phosphorylation of adenosine with borate in formamide.

作者信息

Furukawa Yoshihiro, Kim Hyo-Joong, Hutter Daniel, Benner Steven A

机构信息

1 Department of Earth Science, Graduate School of Science, Tohoku University , Sendai, Japan .

出版信息

Astrobiology. 2015 Apr;15(4):259-67. doi: 10.1089/ast.2014.1209. Epub 2015 Mar 31.

Abstract

Nearly 40 years ago, Schoffstall and his coworkers used formamide as a solvent to permit the phosphorylation of nucleosides by inorganic phosphate to give nucleoside phosphates, which (due to their thermodynamic instability with respect to hydrolysis) cannot be easily created in water by an analogous phosphorylation (the "water problem" in prebiotic chemistry). More recently, we showed that borate could stabilize certain carbohydrates against degradation (the "asphalt problem"). Here, we combine the two concepts to show that borate can work in formamide to guide the reactivity of nucleosides under conditions where they are phosphorylated. Specifically, reaction of adenosine in formamide with inorganic phosphate and pyrophosphate in the presence of borate gives adenosine-5'-phosphate as the only detectable phosphorylated product, with formylation (as opposed to hydrolysis) being the competing reaction.

摘要

近40年前,肖夫斯托尔及其同事使用甲酰胺作为溶剂,使无机磷酸盐对核苷进行磷酸化反应,从而生成核苷磷酸酯。由于它们在水解方面具有热力学不稳定性,因此无法通过类似的磷酸化反应在水中轻易生成(这是前生物化学中的“水问题”)。最近,我们发现硼酸盐可以稳定某些碳水化合物,防止其降解(“沥青问题”)。在此,我们将这两个概念结合起来,表明硼酸盐可以在甲酰胺中发挥作用,在核苷发生磷酸化反应的条件下引导其反应活性。具体而言,在硼酸盐存在的情况下,甲酰胺中的腺苷与无机磷酸盐和焦磷酸盐反应,生成5'-磷酸腺苷作为唯一可检测到的磷酸化产物,而甲酰化反应(与水解反应相反)则是竞争反应。

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