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.
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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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