ArticleNucleic acids research2017
C5-substituents of uridines and 2-thiouridines present at the wobble position of tRNA determine the formation of their keto-enol or zwitterionic forms - a factor important for accuracy of reading of guanosine at the 3΄-end of the mRNA codons.
Article in Nucleic acids research, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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28 citing papers in PubMed, 32 citations in OpenAlex.
- Mechanistic Insights Into the Oxidative Reactivity of 2-Selenouridine in tRNA.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Assessing the contribution of rare DNA states to cancer mutational signatures using sequence-specific conformational fingerprinting.Nature communications · 2026Article
- Recognition of the wobble pair: quantum mechanical calculations of tRNA U34 or C34 modifications within the ribosomal decoding center.Nucleic acids research · 2026Article
- Influence of Phosphate Activation Chemistry on the Selection of the Primordial Genetic Alphabet.Journal of the American Chemical Society · 2026Article
- Translational regulation by oxidative desulfuration of tRNA modifications.Nature communications · 2026Article
- Synthesis and Hybridization Properties of RNA Oligomers Containing Biologically Relevant 5-Aminomethyl-2-thiouridines (xnmCurrent medicinal chemistry · 2026Article
- Uridines Modified with Sulfur or Selenium in U-G Wobble Pairs Matter for tRNA Function.Current medicinal chemistry · 2026Review
- Chalcogen-modified Nucleic Acid Analogues.Current medicinal chemistry · 2026Article
- From U to mnm⁵Se²U: tuning base pairing preferences through 2-chalcogen and 5-methylaminomethyl modifications.Scientific reports · 2025Article
- Assessing the contribution of rare DNA states to cancer mutational signatures using sequence-specific conformational fingerprinting.Research square · 2025Article
- Nonenzymatic RNA copying with a potentially primordial genetic alphabet.Proceedings of the National Academy of Sciences of the United States of America · 2025Article
- Viral codon usage and the virus-host interactions.Frontiers in microbiology · 2025Review
- Protection-Free, Two-step Synthesis of C5-C Functionalized Pyrimidine Nucleosides.Current protocols · 2024Article
- Anionic G•U pairs in bacterial ribosomal rRNAs.RNA (New York, N.Y.) · 2023Article
- The thiolation of uridine 34 in tRNA, which controls protein translation, depends on a [4Fe-4S] cluster in the archaeum Methanococcus maripaludis.Scientific reports · 2023Article
- 2-Selenouridine, a Modified Nucleoside of Bacterial tRNAs, Its Reactivity in the Presence of Oxidizing and Reducing Reagents.International journal of molecular sciences · 2022Article
- Article
- The expanding world of tRNA modifications and their disease relevance.Nature reviews. Molecular cell biology · 2021Review
- Cellular Targeting of Oligonucleotides by Conjugation with Small Molecules.Molecules (Basel, Switzerland) · 2020Review
- dUMP/F-dUMP Binding to Thymidylate Synthase: Human VersusACS omega · 2020Article
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8 authors at 4 institutions in 1 country.
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No grant is acknowledged in the PubMed record.
Abstract
Modified nucleosides present in the wobble position of the tRNA anticodons regulate protein translation through tuning the reading of mRNA codons. Among 40 of such nucleosides, there are modified uridines containing either a sulfur atom at the C2 position and/or a substituent at the C5 position of the nucleobase ring. It is already evidenced that tRNAs with 2-thiouridines at the wobble position preferentially read NNA codons, while the reading mode of the NNG codons by R5U/R5S2U-containing anticodons is still elusive. For a series of 18 modified uridines and 2-thiouridines, we determined the pKa values and demonstrated that both modifying elements alter the electron density of the uracil ring and modulate the acidity of their N3H proton. In aqueous solutions at physiological pH the 2-thiouridines containing aminoalkyl C5-substituents are ionized in ca. 50%. The results, confirmed also by theoretical calculations, indicate that the preferential binding of the modified units bearing non-ionizable 5-substituents to guanosine in the NNG codons may obey the alternative C-G-like (Watson-Crick) mode, while binding of those bearing aminoalkyl C5-substituents (protonated under physiological conditions) and especially those with a sulfur atom at the C2 position, adopt a zwitterionic form and interact with guanosine via a 'new wobble' pattern.
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