Fernandez Garcia, CA;
Grefenstette, NM;
Powner, MW;
(2018)
Selective aqueous acetylation controls the photoanomerization of α-cytidine-5′-phosphate.
Chemical Communications
, 54
(38)
pp. 4850-4853.
10.1039/c8cc01929k.
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Abstract
Nucleic acids are central to information transfer and replication in living systems, providing the molecular foundations of Darwinian evolution. Here we report that prebiotic acetylation of the non-natural, but prebiotically plausible, ribonucleotide α-cytidine-5′-phosphate, selectively protects the vicinal diol moiety. Vicinal diol acetylation blocks oxazolidinone formation and prevents C2′-epimerization upon irradiation with UV-light. Consequently, acetylation enhances (4-fold) the photoanomerization of α-cytidine-5′-phosphate to produce the natural β-pyrimidine ribonucleotide-5′-phosphates required for RNA synthesis.
| Type: | Article |
|---|---|
| Title: | Selective aqueous acetylation controls the photoanomerization of α-cytidine-5′-phosphate |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1039/c8cc01929k |
| Publisher version: | http://dx.doi.org/10.1039/c8cc01929k |
| Language: | English |
| Additional information: | This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (http://creativecommons.org/licenses/by/3.0/). |
| UCL classification: | UCL 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/10047682 |
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