A high-yielding, strictly regioselective prebiotic purine nucleoside formation pathway
A high-yielding, strictly regioselective prebiotic purine nucleoside formation pathway
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DOI：
10.1126/science.aad2808
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发表时间：
2016-05-13
期刊：
影响因子：
56.9
通讯作者：
Carell, Thomas
中科院分区：
文献类型：
--
作者：
Becker, Sidney;Thoma, Ines;Carell, Thomas
人们认为生命的起源始于益生元分子沿着未知的途径反应产生核苷等关键分子。迄今为止，已经提出了嘌呤核苷的单一益生元途径。由于缺乏区域选择性和低产率，它被认为效率低下。我们报道，甲酰胺嘧啶 (FaPys) 与糖的缩合提供了具有极高区域选择性和良好产率 (60%) 的天然 N-9 核苷。 FaPy 可从甲酸和氨基嘧啶中获得，而甲酸和氨基嘧啶又可从罗塞塔彗星任务期间检测到的益生元分子中获得。这种核苷形成途径可以与糖形成反应融合以产生戊糖苷，从而提供了嘌呤核苷在益生元条件下如何形成的合理情景。
The origin of life is believed to have started with prebiotic molecules reacting along unidentified pathways to produce key molecules such as nucleosides. To date, a single prebiotic pathway to purine nucleosides had been proposed. It is considered to be inefficient due to missing regioselectivity and low yields. We report that the condensation of formamidopyrimidines (FaPys) with sugars provides the natural N-9 nucleosides with extreme regioselectivity and in good yields (60%). The FaPys are available from formic acid and aminopyrimidines, which are in turn available from prebiotic molecules that were also detected during the Rosetta comet mission. This nucleoside formation pathway can be fused to sugar-forming reactions to produce pentosides, providing a plausible scenario of how purine nucleosides may have formed under prebiotic conditions.