ArticleJournal of the American Chemical Society2016
A Highly Reactive Imidazolium-Bridged Dinucleotide Intermediate in Nonenzymatic RNA Primer Extension.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 63 papers.
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63 citing papers in PubMed.
- Toward Ideal Proximity-Driven Reactions in Chemical Biology.Chembiochem : a European journal of chemical biology · 2026Review
- Sequence patterns in RNA replication via the virtual circular genome mechanism.Nucleic acids research · 2026Article
- Influence of Phosphate Activation Chemistry on the Selection of the Primordial Genetic Alphabet.Journal of the American Chemical Society · 2026Article
- Complex and Messy Prebiotic Chemistry: Obstacles and Opportunities for an RNA World.Life (Basel, Switzerland) · 2026Review
- Magmatic immiscibility provides phosphate for prebiotic chemistry.Science advances · 2025Article
- Article
- Differential stability and dynamics of DNA-based and RNA-based coacervates affect non-enzymatic RNA chemistry.Nature communications · 2025Article
- Chirality-Promoted Chemical Ligation and Reverse Transcription ofJournal of the American Chemical Society · 2025Article
- Nonenzymatic RNA copying with a potentially primordial genetic alphabet.Proceedings of the National Academy of Sciences of the United States of America · 2025Article
- Monodisperse Chemical Oligophosphorylation of Peptides via Protected Oligophosphorimidazolide Reagents.Angewandte Chemie (International ed. in English) · 2025Article
- Sequencing of d/l-DNA and XNA by Templated-Synthesis.Journal of the American Chemical Society · 2025Article
- On the aqueous origins of the condensation polymers of life.Nature reviews. Chemistry · 2024Review
- 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
- Natural soda lakes provide compatible conditions for RNA and membrane function that could have enabled the origin of life.PNAS nexus · 2024Article
- Unusual Base Pair between Two 2-Thiouridines and Its Implication for Nonenzymatic RNA Copying.Journal of the American Chemical Society · 2024Article
- Insight into the structures of unusual base pairs in RNA complexes containing a primer/template/adenosine ligand.RSC chemical biology · 2023Article
- Rapid Chemical Ligation of DNA andJournal of the American Chemical Society · 2023Article
- Small-Molecule Organocatalysis Facilitates In Situ Nucleotide Activation and RNA Copying.Journal of the American Chemical Society · 2023Article
- Enhanced nonenzymatic RNA copying with in-situ activation of short oligonucleotides.Nucleic acids research · 2023Article
3 more citing papers are in PubMed but not listed here.
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2 authors.
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Abstract
Because of its importance for the origin of life, the nonenzymatic copying of RNA templates has been the subject of intense study for several decades. Previous characterizations of template-directed primer extension using 5'-phosphoryl-2-methylimidazole-activated nucleotides (2-MeImpNs) as substrates have assumed a classical in-line nucleophilic substitution mechanism, in which the 3'-hydroxyl of the primer attacks the phosphate of the incoming monomer, displacing the 2-methylimidazole leaving group. However, we have found that the initial rate of primer extension depends on the pH and concentration at which the activated monomer is maintained prior to the primer extension reaction. These and other results suggest an alternative mechanism, in which two monomers react with each other to form an imidazolium-bridged dinucleotide intermediate, which then binds to the template. Subsequent attack of the 3'-hydroxyl of the primer displaces an activated nucleotide as the leaving group and results in extension of the primer by one nucleotide. Analysis of monomer solutions by NMR indicates formation of the proposed imidazolium-bridged dinucleotide in the expected pH-dependent manner. We have used synthetic methods to prepare material that is enriched in this proposed intermediate and show that it is a highly reactive substrate for primer extension. The formation of an imidazolium-bridged dinucleotide intermediate provides a mechanistic interpretation of previously observed catalysis by an activated nucleotide located downstream from the site of primer extension.
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