ArticleACS chemical biology2012
2'-Azido RNA, a versatile tool for chemical biology: synthesis, X-ray structure, siRNA applications, click labeling.
Article in ACS chemical biology, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 44 papers.
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Who cites it
44 citing papers in PubMed, 109 citations in OpenAlex.
- Oligonucleotides Post-Synthetic Modifications: An Overview of Clickable Nucleoside Phosphoramidites Suitable for Solid-Phase Synthesis.Chembiochem : a European journal of chemical biology · 2026Review
- A Michaelis-Arbuzov-Type Pathway to a Protected 2'-Deoxy-2'-Selenomethyl-Adenosine-3',5'-Phosphoroselenolate Guanosine Dinucleotide for Use in Modified m7G Cap Synthesis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Enzymatic Synthesis of Mixed XNA Polymers Containing 2'Fluoro and 2'Azide Modifications.ACS omega · 2025Article
- Advances and prospects of RNA delivery nanoplatforms for cancer therapy.Acta pharmaceutica Sinica. B · 2025Review
- Synthesis of 2'-formamidonucleoside phosphoramidites for suppressing the seed-based off-target effects of siRNAs.Nucleic acids research · 2024Article
- A Visual Compendium of Principal Modifications within the Nucleic Acid Sugar Phosphate Backbone.Molecules (Basel, Switzerland) · 2024Review
- Nitrogen-Centered Radicals Derived from Azidonucleosides.Molecules (Basel, Switzerland) · 2024Review
- Direct Activation of Nucleobases with Small Molecules for the Conditional Control of Antisense Function.Angewandte Chemie (International ed. in English) · 2024Article
- Synthesis of Peptidyl-tRNA Mimics for Structural Biology Applications.Accounts of chemical research · 2023Review
- Robust synthesis of 2'-azido modified RNA from 2'-amino precursors by diazotransfer reaction.Organic & biomolecular chemistry · 2022Article
- Simple synthesis of massively parallel RNA microarrays via enzymatic conversion from DNA microarrays.Nature communications · 2022Article
- DNA Tiling Enables Precise Acylation-Based Labeling and Control of mRNA.Angewandte Chemie (International ed. in English) · 2021Article
- Strategies for Covalent Labeling of Long RNAs.Chembiochem : a European journal of chemical biology · 2021Review
- Synthesis of Oligoribonucleotides Containing a 2'-Amino-5'-The Journal of organic chemistry · 2021Article
- Triazole-Modified Nucleic Acids for the Application in Bioorganic and Medicinal Chemistry.Biomedicines · 2021Review
- Site of Azido Substitution in the Sugar Moiety of Azidopyrimidine Nucleosides Influences the Reactivity of Aminyl Radicals Formed by Dissociative Electron Attachment.The journal of physical chemistry. B · 2020Article
- Metabolic RNA labeling for probing RNA dynamics in bacteria.Nucleic acids research · 2020Article
- Site-Selective RNA Functionalization via DNA-Induced Structure.Journal of the American Chemical Society · 2020Article
- Cell- and Polymerase-Selective Metabolic Labeling of Cellular RNA with 2'-Azidocytidine.Journal of the American Chemical Society · 2020Article
- Postsynthetic On-Column 2' Functionalization of RNA by Convenient Versatile Method.International journal of molecular sciences · 2020Article
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Authors and funding
8 authors at 2 institutions in 2 countries.
Funding
Abstract
Chemical modification can significantly enrich the structural and functional repertoire of ribonucleic acids and endow them with new outstanding properties. Here, we report the syntheses of novel 2'-azido cytidine and 2'-azido guanosine building blocks and demonstrate their efficient site-specific incorporation into RNA by mastering the synthetic challenge of using phosphoramidite chemistry in the presence of azido groups. Our study includes the detailed characterization of 2'-azido nucleoside containing RNA using UV-melting profile analysis and CD and NMR spectroscopy. Importantly, the X-ray crystallographic analysis of 2'-azido uridine and 2'-azido adenosine modified RNAs reveals crucial structural details of this modification within an A-form double helical environment. The 2'-azido group supports the C3'-endo ribose conformation and shows distinct water-bridged hydrogen bonding patterns in the minor groove. Additionally, siRNA induced silencing of the brain acid soluble protein (BASP1) encoding gene in chicken fibroblasts demonstrated that 2'-azido modifications are well tolerated in the guide strand, even directly at the cleavage site. Furthermore, the 2'-azido modifications are compatible with 2'-fluoro and/or 2'-O-methyl modifications to achieve siRNAs of rich modification patterns and tunable properties, such as increased nuclease resistance or additional chemical reactivity. The latter was demonstrated by the utilization of the 2'-azido groups for bioorthogonal Click reactions that allows efficient fluorescent labeling of the RNA. In summary, the present comprehensive investigation on site-specifically modified 2'-azido RNA including all four nucleosides provides a basic rationale behind the physico- and biochemical properties of this flexible and thus far neglected type of RNA modification.
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