ArticleACS central science2023
Sulfonylation of RNA 2'-OH groups.
Article in ACS central science, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
What it found
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
16 citing papers in PubMed.
- Glutathione-Responsive Acyl-Modifications for Targeted RNA Decaging and Prolonged Protein Synthesis.Angewandte Chemie (International ed. in English) · 2026Article
- SuFEx chemistry for nucleosides, nucleotides, and nucleic acids.RSC chemical biology · 2026Review
- Mechanistically Defined Epoxide- and Aziridine-2-carboxamide Electrophiles Enable Stereoselective Covalent Ribonucleic Acid Modulation.Journal of the American Chemical Society · 2026Article
- Recent Advances in Chemical Probing Strategies for RNA Structure Determination In Vivo.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Fluorogenic Covalent Probes for RNA.Journal of the American Chemical Society · 2025Article
- Sequence-Specific Installation of Aryl Groups in RNA via DNA-Catalyst Conjugates.Angewandte Chemie (International ed. in English) · 2025Article
- Sulfonylation sites for adenine and its nucleosides/nucleotides.Journal of pharmaceutical analysis · 2025Article
- Article
- Discovery of Macrocyclic Peptide Binders, Covalent Modifiers, and Degraders of a Structured RNA by mRNA Display.Journal of the American Chemical Society · 2025Article
- Advances in sulfonyl exchange chemical biology: expanding druggable target space.Chemical science · 2025Review
- Selective Arylation of RNA 2'-OH Groups via SAngewandte Chemie (International ed. in English) · 2024Article
- Second-Generation Chiral Amino Acid Derivatives Afford High Stereoselectivity and Stability in Aqueous RNA Acylation.The Journal of organic chemistry · 2024Article
- Aqueous Activation of RNA 2'-OH for Conjugation with Amines and Thiols.Bioconjugate chemistry · 2024Article
- Efficient post-synthesis incorporation and conjugation of reactive ketones in RNAChemical communications (Cambridge, England) · 2023Article
- Covalent Stapling of the Cereblon Sensor Loop Histidine Using Sulfur-Heterocycle Exchange.ACS medicinal chemistry letters · 2023Article
- Purification of linearized template plasmid DNA decreases double-stranded RNA formation during IVT reaction.Frontiers in molecular biosciences · 2023Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
The nucleophilic reactivity of RNA 2'-OH groups in water has proven broadly useful in probing, labeling, and conjugating RNA. To date, reactions selective to ribose 2'-OH have been limited to bond formation with short-lived carbonyl electrophiles. Here we report that many activated small-molecule sulfonyl species can exhibit extended lifetimes in water and retain 2'-OH reactivity. The data establish favorable aqueous solubility for selected reagents and successful RNA-selective reactions at stoichiometric and superstoichiometric yields, particularly for aryl sulfonyltriazole species. We report that the latter are considerably more stable than most prior carbon electrophiles in aqueous environments and tolerate silica chromatography. Furthermore, an azide-substituted sulfonyltriazole reagent is developed to introduce labels into RNA via click chemistry. In addition to high-yield reactions, we find that RNA sulfonylation can also be performed under conditions that give trace yields necessary for structure mapping. Like acylation, the reaction occurs with selectivity for unpaired nucleotides over those in the duplex structure, and a sulfonate adduct causes reverse transcriptase stops, suggesting potential use in RNA structure analysis. Probing of rRNA is demonstrated in human cells, indicating possible cell permeability. The sulfonyl reagent class enables a new level of control, selectivity, versatility, and ease of preparation for RNA applications.
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Registered trials
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.