ArticleMolecules (Basel, Switzerland)2013
Oligonucleotide tagging for copper-free click conjugation.
Article in Molecules (Basel, Switzerland), 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 34 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
- Synthesis and stability studies of bicyclo[6.1.0]nonyne scaffolds for automated solid-phase oligonucleotide synthesis.RSC advances · 2024Article
- Bicyclo[6.1.0]nonyne carboxylic acid for the production of stable molecular probes.RSC advances · 2021Article
- Triazole-Modified Nucleic Acids for the Application in Bioorganic and Medicinal Chemistry.Biomedicines · 2021Review
- Covalent labeling of nucleic acids.Chemical Society reviews · 2020Review
- Detecting individual extracellular vesicles using a multicolor in situ proximity ligation assay with flow cytometric readout.Scientific reports · 2016Article
- Strain Promoted Click Chemistry of 2- or 8-Azidopurine and 5-Azidopyrimidine Nucleosides and 8-Azidoadenosine Triphosphate with Cyclooctynes. Application to Living Cell Fluorescent Imaging.Bioconjugate chemistry · 2015Article
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Authors and funding
8 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Copper-free click chemistry between cyclooctynes and azide is a mild, fast and selective technology for conjugation of oligonucleotides. However, technology for site-specific introduction of the requisite probes by automated protocols is scarce, while the reported cyclooctynes are large and hydrophobic. In this work, it is demonstrated that the introduction of bicyclo[6.1.0]nonyne (BCN) into synthetic oligonucleotides is feasible by standard solid-phase phosphoramidite chemistry. A range of phosphoramidite building blocks is presented for incoporation of BCN or azide, either on-support or in solution. The usefulness of the approach is demonstrated by the straightforward and high-yielding conjugation of the resulting oligonucleotides, including biotinylation, fluorescent labeling, dimerization and attachment to polymer.
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Registered trials
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