ArticleNature chemistry2022
Prebiotic synthesis and triphosphorylation of 3'-amino-TNA nucleosides.
Article in Nature chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 14 citations in OpenAlex.
- Controlled Formation and Unusual Reactivity of Cyanohexatriyne (HCChemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- From searching for extraterrestrial biosignatures to exploring the origins of life: A prebiotic chemistry perspective.Fundamental research · 2026Review
- Molecular war and peace: the concurrent path to antibiosis and antibiotic resistance.Frontiers in microbiology · 2026Review
- On the aqueous origins of the condensation polymers of life.Nature reviews. Chemistry · 2024Review
- A Prebiotic Genetic Nucleotide as an Early Darwinian Ancestor for Pre-RNA Evolution.ACS omega · 2024Article
- Photochemistry of 2-thiooxazole: a plausible prebiotic precursor to RNA nucleotides.Physical chemistry chemical physics : PCCP · 2022Article
- Making nucleic acid monomers.Nature chemistry · 2022Article
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Authors and funding
2 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Nucleosides are essential to the emergence of life, and so their synthesis is a key challenge for prebiotic chemistry. Although amino-nucleosides have enhanced reactivity in water compared with ribonucleosides, they are assumed to be prebiotically irrelevant due to perceived difficulties with their selective formation. Here we demonstrate that 3'-amino-TNA nucleosides (TNA, threose nucleic acid) are formed diastereoselectively and regiospecifically from prebiotic feedstocks in four high-yielding steps. Phosphate provides an unexpected resolution, leading to spontaneous purification of the genetically relevant threo-isomer. Furthermore, 3'-amino-TNA nucleosides are shown to be phosphorylated directly in water, under mild conditions with cyclic trimetaphosphate, forming a nucleoside triphosphate (NTP) in a manner not feasible for canonical nucleosides. Our results suggest 3'-amino-TNA nucleosides may have been present on the early Earth, and the ease with which these NTPs form, alongside the inherent selectivity for the Watson-Crick base-pairing threo-monomer, warrants further study of the role they could play during the emergence of life.
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