Selective Prebiotic Synthesis of a-Threofuranosyl Cytidine by Photochemical Anomerization
Selective Prebiotic Synthesis of a-Threofuranosyl Cytidine by Photochemical Anomerization
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光化学异构化选择性益生元合成α-苏呋喃糖基胞苷
DOI：
10.1002/ange.202101376
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发表时间：
2021
影响因子：
--
通讯作者：
Colville B
中科院分区：
文献类型：
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作者：
Colville B
生命中第一个基因聚合物的结构是一个持续激烈争论的问题。 “RNA世界理论”表明RNA是生命的第一个核酸。然而，核糖核苷酸是复杂的化学结构，而更简单的核酸，例如苏糖核酸（TNA），可以携带遗传信息。原则上，像 TNA 这样的核酸可能在生命起源中发挥着至关重要的作用。生命中任何基因聚合物的出现都需要其单体的合成。在这里，我们展示了苏式胞苷 3（TNA 的重要组成部分）的高产、立体、区域和呋喃糖基选择性益生元合成。我们的合成使用了先前在经典嘧啶核糖核苷胞苷1的益生元合成中使用的关键中间体和反应。此外，我们证明红细胞特异性 2',3'-环状磷酸盐合成提供了一种光化学选择 TNA 胞苷的机制。这些结果表明，在生命出现期间，TNA 可能与 RNA 共存。
The structure of life's first genetic polymer is a question of intense ongoing debate. The “RNA world theory” suggests RNA was life's first nucleic acid. However, ribonucleotides are complex chemical structures, and simpler nucleic acids, such as threose nucleic acid (TNA), can carry genetic information. In principle, nucleic acids like TNA could have played a vital role in the origins of life. The advent of any genetic polymer in life requires synthesis of its monomers. Here we demonstrate a high‐yielding, stereo‐, regio‐ and furanosyl‐selective prebiotic synthesis of threo‐cytidine3, an essential component of TNA. Our synthesis uses key intermediates and reactions previously exploited in the prebiotic synthesis of the canonical pyrimidine ribonucleoside cytidine1. Furthermore, we demonstrate that erythro‐specific 2′,3′‐cyclic phosphate synthesis provides a mechanism to photochemically select TNA cytidine. These results suggest that TNA may have coexisted with RNA during the emergence of life.