ArticleNature chemistry2017
A prebiotically plausible synthesis of pyrimidine β-ribonucleosides and their phosphate derivatives involving photoanomerization.
Article in Nature chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 69 papers.
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69 citing papers in PubMed.
- Continuous UV irradiation played an inconclusive role in selecting the canonical genetic alphabet.Proceedings of the National Academy of Sciences of the United States of America · 2026Article
- WAngewandte Chemie (International ed. in English) · 2026Article
- Influence of Phosphate Activation Chemistry on the Selection of the Primordial Genetic Alphabet.Journal of the American Chemical Society · 2026Article
- A scope of prebiotic neat reaction conditions and the mechanism of urea-assisted phosphorylations of alcohols.Nature communications · 2025Article
- One-Pot Synthesis of Novel Pyrimidine Derivatives with Potential Antidiabetic Activity Through Dual α-Glucosidase and α-Amylase Inhibitors.Molecules (Basel, Switzerland) · 2025Article
- Preferential survival of prebiotic metallopeptides in the presence of ultraviolet light.Chemical science · 2025Article
- Review
- Stereoselectivity of Aminoacyl-RNA Loop-Closing Ligation.Journal of the American Chemical Society · 2025Article
- Nonenzymatic RNA copying with a potentially primordial genetic alphabet.Proceedings of the National Academy of Sciences of the United States of America · 2025Article
- A tRNA modification with aminovaleramide facilitates AUA decoding in protein synthesis.Nature chemical biology · 2025Article
- The Effect of Sulphur Atom on the Structure of Biomolecule 2-Thiocytosine in the Gas-Phase, Solid-State, and Hydrated Forms and in DNA-DNA Microhelices as Compared to Canonical Ones.Molecules (Basel, Switzerland) · 2025Article
- Stem Life: A Framework for Understanding the Prebiotic-Biotic Transition.Journal of molecular evolution · 2024Article
- Prebiotic synthesis of dihydrouridine by photoreduction of uridine in formamide.Chemical communications (Cambridge, England) · 2024Article
- Article
- Unusual Base Pair between Two 2-Thiouridines and Its Implication for Nonenzymatic RNA Copying.Journal of the American Chemical Society · 2024Article
- Photoinduced charge separation and DNA self-repair depend on sequence directionality and stacking pattern.Chemical science · 2024Article
- Chirality-induced avalanche magnetization of magnetite by an RNA precursor.Nature communications · 2023Article
- Thiophosphate photochemistry enables prebiotic access to sugars and terpenoid precursors.Nature chemistry · 2023Article
- The central dogma of biological homochirality: How does chiral information propagate in a prebiotic network?The Journal of chemical physics · 2023Article
- On the origin of life: an RNA-focused synthesis and narrative.RNA (New York, N.Y.) · 2023Article
9 more citing papers are in PubMed but not listed here.
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8 authors.
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Abstract
Previous research has identified ribose aminooxazoline as a potential intermediate in the prebiotic synthesis of the pyrimidine nucleotides with remarkable properties. It crystallizes spontaneously from reaction mixtures, with an enhanced enantiomeric excess if initially enantioenriched, which suggests that reservoirs of this compound might have accumulated on the early Earth in an optically pure form. Ribose aminooxazoline can be converted efficiently into α-ribocytidine by way of 2,2'-anhydroribocytidine, although anomerization to β-ribocytidine by ultraviolet irradiation is extremely inefficient. Our previous work demonstrated the synthesis of pyrimidine β-ribonucleotides, but at the cost of ignoring ribose aminooxazoline, using arabinose aminooxazoline instead. Here we describe a long-sought route through ribose aminooxazoline to the pyrimidine β-ribonucleosides and their phosphate derivatives that involves an extraordinarily efficient photoanomerization of α-2-thioribocytidine. In addition to the canonical nucleosides, our synthesis accesses β-2-thioribouridine, a modified nucleoside found in transfer RNA that enables both faster and more-accurate nucleic acid template-copying chemistry.
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