ArticleBioorganic & medicinal chemistry2012
Covalent protein-oligonucleotide conjugates by copper-free click reaction.
Article in Bioorganic & medicinal chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
- One-Pot Enzymatic ADDing of Click Chemistry Handles for Protein Immobilization and Bioconjugation of Small and Biomolecules.Bioconjugate chemistry · 2026Article
- Engineering protein prenylation: an emerging tool for selective protein modification.Biochemical Society transactions · 2025Review
- Reactivity Profiling for High-Yielding Ynamine-Tagged Oligonucleotide Click Chemistry Bioconjugations.Bioconjugate chemistry · 2024Article
- Library Screening, In Vivo Confirmation, and Structural and Bioinformatic Analysis of Pentapeptide Sequences as Substrates for Protein Farnesyltransferase.International journal of molecular sciences · 2024Article
- Micropreparative Gel Electrophoresis for Purification of Nanoscale Bioconjugates.Bioconjugate chemistry · 2024Article
- Synthesis, Enzymatic Peptide Incorporation, and Applications of Diazirine-Containing Isoprenoid Diphosphate Analogues.Organic letters · 2023Article
- MALDI-MS Analysis of Peptide Libraries Expands the Scope of Substrates for Farnesyltransferase.International journal of molecular sciences · 2021Article
- Herding cats: Label-based approaches in protein translocation through nanopore sensors for single-molecule protein sequence analysis.iScience · 2021Review
- Synthesis of Multi-Protein Complexes through Charge-Directed Sequential Activation of Tyrosine Residues.Journal of the American Chemical Society · 2021Article
- A Not-So-Ancient Grease History: Click Chemistry and Protein Lipid Modifications.Chemical reviews · 2021Review
- DNA-Scaffolded Proximity Assembly and Confinement of Multienzyme Reactions.Topics in current chemistry (Cham) · 2020Review
- Efficient bioactive oligonucleotide-protein conjugation for cell-targeted cancer therapy.ChemistryOpen · 2019Article
- Covalent "Click Chemistry"-Based Attachment of DNA onto Solid Phase Enables Iterative Molecular Analysis.Analytical chemistry · 2019Article
- Recent progress in enzymatic protein labelling techniques and their applications.Chemical Society reviews · 2018Review
- In situ protein detection with enhanced specificity using DNA-conjugated antibodies and proximity ligation.Modern pathology : an official journal of the United States and Canadian Academy of Pathology, Inc · 2018Article
- Protein prenylation: enzymes, therapeutics, and biotechnology applications.ACS chemical biology · 2015Review
- Synthesis of site-specific DNA-protein conjugates and their effects on DNA replication.ACS chemical biology · 2014Article
- Enzymatic labeling of proteins: techniques and approaches.Bioconjugate chemistry · 2013Review
- Oligonucleotide tagging for copper-free click conjugation.Molecules (Basel, Switzerland) · 2013Article
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Authors and funding
7 authors.
Funding
Abstract
Covalent protein-oligodeoxynucleotide (protein-ODN) conjugates are useful in a number of biological applications, but synthesizing discrete conjugates-where the connection between the two components is at a defined location in both the protein and the ODN-under mild conditions with significant yield can be a challenge. In this article, we demonstrate a strategy for synthesizing discrete protein-ODN conjugates using strain-promoted azide-alkyne [3+2] cycloaddition (SPAAC, a copper-free 'click' reaction). Azide-functionalized proteins, prepared by enzymatic prenylation of C-terminal CVIA tags with synthetic azidoprenyl diphosphates, were 'clicked' to ODNs that had been modified with a strained dibenzocyclooctyne (DIBO-ODN). The resulting protein-ODN conjugates were purified and characterized by size-exclusion chromatography and gel electrophoresis. We find that the yields and reaction times of the SPAAC bioconjugation reactions are comparable to those previously reported for copper-catalyzed azide-alkyne [3+2] cycloaddition (CuAAC) bioconjugation, but require no catalyst. The same SPAAC chemistry was used to immobilize azide-modified proteins onto surfaces, using surface-bound DIBO-ODN as a heterobifunctional linker. Cu-free click bioconjugation of proteins to ODNs is a simple and versatile alternative to Cu-catalyzed click methods.
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