Nucleoside Azide-Alkyne Cycloaddition Reactions Under Solvothermal Conditions or Using Copper Vials in a Ball Mill

Andrew J. Cummings, Francesco Ravalico, Kegan I. S. McColgan-Bannon, Olga Eguaogie, P. Alain Elliott, Matthew R. Shannon, Iris A. Bermejo, Angus Dwyer, Amanda B. Maginty, James Mack, Joseph S. Vyle

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9 Citations (Scopus)

Abstract

Novel nucleoside analogues containing photoswitchable moieties were prepared using 'click' cycloaddition reactions between 5 '-azido-5 '-deoxythymidine and mono- or bis-N-propargylamide-substituted azobenzenes. In solution, high to quantitative yields were achieved using 5mol% Cu(I) in the presence of a stabilizing ligand. 'Click' reactions using the monopropargylamides were also effected in the absence of added cuprous salts by the application of liquid assisted grinding (LAG) in metallic copper reaction vials. Specifically, high speed vibration ball milling (HSVBM) using a 3/32('') (2.38mm) diameter copper ball (62mg) at 60Hz overnight in the presence of ethyl acetate lead to complete consumption of the 5 '-azido nucleoside with clean conversion to the corresponding 1,3-triazole.
Original languageEnglish
Pages (from-to)361-370
Number of pages10
JournalNucleosides, Nucleotides and Nucleic Acids
Volume34
Issue number5
DOIs
Publication statusPublished - 15 Apr 2015

Keywords

  • TERMINAL ALKYNES
  • CLICK CHEMISTRY
  • SOLVENT-FREE
  • DNA
  • NANOPARTICLES
  • PROTECTION

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    Cummings, A. J., Ravalico, F., McColgan-Bannon, K. I. S., Eguaogie, O., Elliott, P. A., Shannon, M. R., Bermejo, I. A., Dwyer, A., Maginty, A. B., Mack, J., & Vyle, J. S. (2015). Nucleoside Azide-Alkyne Cycloaddition Reactions Under Solvothermal Conditions or Using Copper Vials in a Ball Mill. Nucleosides, Nucleotides and Nucleic Acids, 34(5), 361-370. https://doi.org/10.1080/15257770.2014.1001855