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Selective Prebiotic Synthesis of α‐Threofuranosyl Cytidine by Photochemical Anomerization

Colville, BWF; Powner, MW; (2021) Selective Prebiotic Synthesis of α‐Threofuranosyl Cytidine by Photochemical Anomerization. Angewandte Chemie 10.1002/ange.202101376. (In press). Green open access

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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.

Type: Article
Title: Selective Prebiotic Synthesis of α‐Threofuranosyl Cytidine by Photochemical Anomerization
Open access status: An open access version is available from UCL Discovery
DOI: 10.1002/ange.202101376
Publisher version: https://doi.org/10.1002/ange.202101376
Language: English
Additional information: © 2021 The Authors. Angewandte Chemie published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/).
Keywords: nucleotides, origin of life, photochemistry, prebiotic chemistry, TNA
UCL classification: UCL
UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > UCL BEAMS
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
URI: https://discovery.ucl.ac.uk/id/eprint/10125505
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