Selective aqueous acetylation controls the photoanomerization of $α$-cytidine-5′-phosphate

Selective aqueous acetylation controls the photoanomerization of $α$-cytidine-5′-phosphate. Fernández-García, C., Grefenstette, N. M., & Powner, M. W. Chemical Communications, 54(38):4850–4853, 2018.
doi abstract bibtex

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.

@article{Fernandez-Garcia2018,
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 $\alpha$-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 $\alpha$-cytidine-5′-phosphate to produce the natural $\beta$-pyrimidine ribonucleotide-5′-phosphates required for RNA synthesis.},
author = {Fern{\'{a}}ndez-Garc{\'{i}}a, Christian and Grefenstette, Natalie M. and Powner, Matthew W.},
doi = {10.1039/c8cc01929k},
issn = {1364548X},
journal = {Chemical Communications},
number = {38},
pages = {4850--4853},
pmid = {29697101},
title = {{Selective aqueous acetylation controls the photoanomerization of $\alpha$-cytidine-5′-phosphate}},
volume = {54},
year = {2018}
}

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