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Prebiotic synthesis and triphosphorylation of 3′-amino-TNA nucleosides

Powner, Matthew; Whitaker, Daniel; (2022) Prebiotic synthesis and triphosphorylation of 3′-amino-TNA nucleosides. Nature Chemistry , 14 pp. 766-774. 10.1038/s41557-022-00982-5. Green open access

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Abstract

Nucleosides are essential to the emergence of life, and so their synthesis is a key challenge for prebiotic chemistry. Whilst 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 3′-amino-TNA nucleosides 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.

Type: Article
Title: Prebiotic synthesis and triphosphorylation of 3′-amino-TNA nucleosides
Open access status: An open access version is available from UCL Discovery
DOI: 10.1038/s41557-022-00982-5
Publisher version: https://doi.org/10.1038/s41557-022-00982-5
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
Keywords: Nucleic acids, Nucleotides, Phosphorylation, Origins of Life, Prebiotic Chemistry, Organic Chemistry
UCL classification: UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL
URI: https://discovery.ucl.ac.uk/id/eprint/10150798
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