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

Autor: Fernández-García, Christian, Grefenstette, Natalie M., Powner, Matthew W.
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Zdroj: Chemical Communications; 5/11/2018, Vol. 54 Issue 38, p4850-4853, 4p
Abstrakt: 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. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index