ArticleAngewandte Chemie (International ed. in English)2021
Selective Prebiotic Synthesis of α-Threofuranosyl Cytidine by Photochemical Anomerization.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed, 18 citations in OpenAlex.
- On-Demand Photoprotection by UV-Transparent Small Molecules via Aggregation-Induced Absorption: The Origin and Modern Application.ACS central science · 2026Article
- Detection of a four-carbon sugar in interstellar space.Nature astronomy · 2026Article
- On the aqueous origins of the condensation polymers of life.Nature reviews. Chemistry · 2024Review
- Constraints on the emergence of RNA through non-templated primer extension with mixtures of potentially prebiotic nucleotides.Nucleic acids research · 2024Article
- Photoinduced charge separation and DNA self-repair depend on sequence directionality and stacking pattern.Chemical science · 2024Article
- Towards a prebiotic chemoton - nucleotide precursor synthesis driven by the autocatalytic formose reaction.Chemical science · 2023Article
- Thermodynamic and Kinetic Sequence Selection in Enzyme-Free Polymer Self-Assembly inside a Non-equilibrium RNA Reactor.Life (Basel, Switzerland) · 2022Article
- An RNA-cleaving threose nucleic acid enzyme capable of single point mutation discrimination.Nature chemistry · 2022Article
- Ribose Alters the Photochemical Properties of the Nucleobase in Thionated Nucleosides.The journal of physical chemistry letters · 2021Article
- Selective Prebiotic Synthesis of α-Threofuranosyl Cytidine by Photochemical Anomerization.Angewandte Chemie (International ed. in English) · 2021Article
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2 authors at 1 institution in 1 country.
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Abstract
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-cytidine 3, an essential component of TNA. Our synthesis uses key intermediates and reactions previously exploited in the prebiotic synthesis of the canonical pyrimidine ribonucleoside cytidine 1. 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.
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