ArticleJournal of the American Chemical Society2013
Synthesis of N3'-P5'-linked phosphoramidate DNA by nonenzymatic template-directed primer extension.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed, 50 citations in OpenAlex.
- A Facile Strategy for 3'-Terminal Functionalization of DNA and RNA via On-Column Conjugation with Integration into Tandem Oligonucleotide Synthesis.Current protocols · 2026Article
- Derivatization of Solid Supports Using a Carbamate-Linked Tether Containing a Disulfide Functional Group.Current protocols · 2025Article
- A Versatile Disulfide-Containing Solid-Support Strategy for 3'-Modifiers in Oligonucleotides: Introducing Modular Tandem Oligonucleotide Synthesis.Chemistry, an Asian journal · 2025Article
- An Aqueous-Compatible On-Column Approach for the Conjugation of Nucleic Acids Using Amino Modifiers.Current protocols · 2025Article
- Aqueous Compatible Post-Synthetic On-Column Conjugation of Nucleic Acids Using Amino-Modifiers.Chembiochem : a European journal of chemical biology · 2025Article
- A Ribonucleotide ↔ Phosphoramidate Reaction Network Optimized by Computer-Aided Design.Journal of the American Chemical Society · 2022Article
- Structure-Activity Relationships in Nonenzymatic Template-Directed RNA Synthesis.Angewandte Chemie (International ed. in English) · 2021Article
- A Potential Role for Aminoacylation in Primordial RNA Copying Chemistry.Biochemistry · 2021Article
- Assembly of a Ribozyme Ligase from Short Oligomers by Nonenzymatic Ligation.Journal of the American Chemical Society · 2020Article
- Nonenzymatic RNA-templated Synthesis of N3'→P5' Phosphoramidate DNA.Bio-protocol · 2020Article
- Template-Directed Copying of RNA by Non-enzymatic Ligation.Angewandte Chemie (International ed. in English) · 2020Article
- Synthesis of phosphoramidate-linked DNA by a modified DNA polymerase.Proceedings of the National Academy of Sciences of the United States of America · 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
- Stereoselective Syntheses of 3'-Hydroxyamino- and 3'-Methoxyamino-2',3'-Dideoxynucleosides.Organic letters · 2019Article
- Article
- DNA polymerase activity on synthetic N3'→P5' phosphoramidate DNA templates.Nucleic acids research · 2019Article
- Template-Directed Nonenzymatic Primer Extension Using 2-Methylimidazole-Activated Morpholino Derivatives of Guanosine and Cytidine.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
- The Chemical Likelihood of Ribonucleotide-α-Amino acid Copolymers as Players for Early Stages of Evolution.Journal of molecular evolution · 2019Article
- Enzyme-free genetic copying of DNA and RNA sequences.Beilstein journal of organic chemistry · 2018Review
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
Abstract
A fast and accurate pathway for nonenzymatic RNA replication would simplify models for the emergence of the RNA world from the prebiotic chemistry of the early earth. However, numerous difficulties stand in the way of an experimental demonstration of effective nonenzymatic RNA replication. To gain insight into the necessary properties of potentially self-replicating informational polymers, we have studied several model systems based on amino-sugar nucleotides. Here we describe the synthesis of N3'-P5'-linked phosphoramidate DNA (3'-NP-DNA) by the template-directed polymerization of activated 3'-amino-2',3'-dideoxyribonucleotides. 3'-NP-DNA is an interesting model because of its very RNA-like A-type duplex conformation and because activated 3'-amino-2',3'-dideoxyribonucleotides are much more reactive than the corresponding activated ribonucleotides. In contrast to our previous studies with 2'-amino-2',3'-dideoxyribonucleotides (for which G and C but not A and T exhibit efficient template copying), we have found that all four canonical 3'-amino-2',3'-dideoxyribonucleotides (G, C, A, and T) polymerize efficiently on RNA templates. RNA templates are generally superior to DNA templates, and oligo-ribo-T templates are superior to oligo-ribo-U templates, which are the least efficient of the RNA homopolymer templates. We have also found that activation of 3'-aminonucleotides with 2-methylimidazole results in a ca. 10-fold higher polymerization rate relative to activation with imidazole, an observation that parallels earlier findings with ribonucleotides. We discuss the implications of our experiments for the possibility of self-replication in the 3'-NP-DNA and RNA systems.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.