ArticleNucleic acids research2021
Impact of 3-deazapurine nucleobases on RNA properties.
Article in Nucleic acids research, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed, 16 citations in OpenAlex.
- Origins of Reactivity in SAM-Utilizing Ribozyme SAMURI-Catalyzed RNA Alkylation.Journal of the American Chemical Society · 2026Article
- 1-Deazainosine-impact on RNA structure and role in exploring ribozyme catalysis.Chemical science · 2026Article
- A magic methyl effect in the active site of a methyltransferase ribozyme.Nature communications · 2026Article
- Article
- The intrinsic preference of guanosine bases for cleavage-facilitating interactions with phosphodiester moieties in RNA anions revealed by base modifications and mass spectrometry.Nucleic acids research · 2025Article
- The Tautomeric State ofACS central science · 2024Article
- A SAM analogue-utilizing ribozyme for site-specific RNA alkylation in living cells.Nature chemistry · 2023Article
- Calculated pThe journal of physical chemistry. A · 2023Article
- Tailored Tolane-Perfluorotolane Assembly as Supramolecular Base Pair Replacement in DNA.Angewandte Chemie (International ed. in English) · 2023Article
- Scaling Catalytic Contributions of Small Self-Cleaving Ribozymes.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Article
- Scaling Catalytic Contributions of Small Self-Cleaving Ribozymes.Angewandte Chemie (International ed. in English) · 2022Article
- A High-Pressure, High-Temperature Flow Reactor Simulating the Hadean Earth Environment, with Application to the Pressure Dependence of the Cleavage of Avocado Viroid Hammerhead Ribozyme.Life (Basel, Switzerland) · 2022Article
- 1-Deazaguanosine-Modified RNA: The Missing Piece for Functional RNA Atomic Mutagenesis.Journal of the American Chemical Society · 2022Article
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Authors and funding
9 authors at 2 institutions in 2 countries.
Funding
Abstract
Deazapurine nucleosides such as 3-deazaadenosine (c3A) are crucial for atomic mutagenesis studies of functional RNAs. They were the key for our current mechanistic understanding of ribosomal peptide bond formation and of phosphodiester cleavage in recently discovered small ribozymes, such as twister and pistol RNAs. Here, we present a comprehensive study on the impact of c3A and the thus far underinvestigated 3-deazaguanosine (c3G) on RNA properties. We found that these nucleosides can decrease thermodynamic stability of base pairing to a significant extent. The effects are much more pronounced for 3-deazapurine nucleosides compared to their constitutional isomers of 7-deazapurine nucleosides (c7G, c7A). We furthermore investigated base pair opening dynamics by solution NMR spectroscopy and revealed significantly enhanced imino proton exchange rates. Additionally, we solved the X-ray structure of a c3A-modified RNA and visualized the hydration pattern of the minor groove. Importantly, the characteristic water molecule that is hydrogen-bonded to the purine N3 atom and always observed in a natural double helix is lacking in the 3-deazapurine-modified counterpart. Both, the findings by NMR and X-ray crystallographic methods hence provide a rationale for the reduced pairing strength. Taken together, our comparative study is a first major step towards a comprehensive understanding of this important class of nucleoside modifications.
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