ArticleJournal of the American Chemical Society2017
A Mechanistic Explanation for the Regioselectivity of Nonenzymatic RNA Primer Extension.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- MgJournal of the American Chemical Society · 2026Article
- The XNA alphabet.Nucleic acids research · 2025Review
- Overcoming nucleotide bias in the nonenzymatic copying of RNA templates.Nucleic acids research · 2024Article
- Simulations predict preferred MgBiophysical journal · 2024Article
- Constraints on the emergence of RNA through non-templated primer extension with mixtures of potentially prebiotic nucleotides.Nucleic acids research · 2024Article
- Phosphorylation in liquid sulfur dioxide under prebiotically plausible conditions.Communications chemistry · 2022Article
- Peptides before and during the nucleotide world: an origins story emphasizing cooperation between proteins and nucleic acids.Journal of the Royal Society, Interface · 2022Review
- Competition between bridged dinucleotides and activated mononucleotides determines the error frequency of nonenzymatic RNA primer extension.Nucleic acids research · 2021Article
- 2'/3' Regioselectivity of Enzyme-Free Copying of RNA Detected by NMR.Chembiochem : a European journal of chemical biology · 2020Article
- Deep sequencing of non-enzymatic RNA primer extension.Nucleic acids research · 2020Article
- A Model for the Emergence of RNA from a Prebiotically Plausible Mixture of Ribonucleotides, Arabinonucleotides, and 2'-Deoxynucleotides.Journal of the American Chemical Society · 2020Article
- Prebiotically Plausible "Patching" of RNA Backbone Cleavage through a 3'-5' Pyrophosphate Linkage.Journal of the American Chemical Society · 2019Article
- Nonenzymatic Template-Directed Synthesis of Mixed-Sequence 3'-NP-DNA up to 25 Nucleotides Long Inside Model Protocells.Journal of the American Chemical Society · 2019Article
- Article
- Copying of Mixed-Sequence RNA Templates inside Model Protocells.Journal of the American Chemical Society · 2018Article
- Structural Rationale for the Enhanced Catalysis of Nonenzymatic RNA Primer Extension by a Downstream Oligonucleotide.Journal of the American Chemical Society · 2018Article
- Synthesis of a Nonhydrolyzable Nucleotide Phosphoroimidazolide Analogue That Catalyzes Nonenzymatic RNA Primer Extension.Journal of the American Chemical Society · 2018Article
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5 authors.
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Abstract
A working model of nonenzymatic RNA primer extension could illuminate how prebiotic chemistry transitioned to biology. All currently known experimental reconstructions of nonenzymatic RNA primer extension yield a mixture of 2'-5' and 3'-5' internucleotide linkages. Although long seen as a major problem, the causes of the poor regioselectivity of the reaction are unknown. We used a combination of different leaving groups, nucleobases, and templating sequences to uncover the factors that yield selective formation of 3'-5' internucleotide linkages. We found that fast and high yielding reactions selectively form 3'-5' linkages. Additionally, in all cases with high 3'-5' regioselectivity, Watson-Crick base pairing between the RNA monomers and the template is observed at the extension site and at the adjacent downstream position. Mismatched base-pairs and other factors that would perturb the geometry of the imidazolium bridged intermediate lower both the rate and regioselectivity of the reaction.
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