ArticleNature communications2023
Synthesis of tertiary alkylphosphonate oligonucleotides through light-driven radical-polar crossover reactions.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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
6 citing papers in PubMed.
- Iron-Photocatalyzed C(spAngewandte Chemie (International ed. in English) · 2026Article
- Organophotoredox-Catalyzed Postfunctionalization of Poly(methacrylate) Derivatives via Radical-Polar Crossover Phosphonylation.Angewandte Chemie (International ed. in English) · 2025Article
- Catalytic Reductive Homocoupling of Benzyl Chlorides Enabled by Zirconocene and Photoredox Catalysis.Precision chemistry · 2025Article
- Chemical strategies for antisense antibiotics.Chemical Society reviews · 2024Review
- Synthesis, Biophysical and Biological Evaluation of Splice-Switching Oligonucleotides with Multiple LNA-Phosphothiotriester Backbones.Journal of the American Chemical Society · 2024Article
- Development of a General Organophosphorus Radical Trap: Deoxyphosphonylation of Alcohols.Journal of the American Chemical Society · 2024Article
Corrections and comments
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Authors and funding
10 authors.
Funding
Abstract
Chemical modification of nucleotides can improve the metabolic stability and target specificity of oligonucleotide therapeutics, and alkylphosphonates have been employed as charge-neutral replacements for naturally-occurring phosphodiester backbones in these compounds. However, at present, the alkyl moieties that can be attached to phosphorus atoms in these compounds are limited to methyl groups or primary/secondary alkyls, and such alkylphosphonate moieties can degrade during oligonucleotide synthesis. The present work demonstrates the tertiary alkylation of the phosphorus atoms of phosphites bearing two 2'-deoxynuclosides. This process utilizes a carbocation generated via a light-driven radical-polar crossover mechanism. This protocol provides tertiary alkylphosphonate structures that are difficult to synthesize using existing methods. The conversion of these species to oligonucleotides having charge-neutral alkylphosphonate linkages through a phosphoramidite-based approach was also confirmed in this study.
Identifiers
What OpenQuestion holds
Registered trials
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