Hypoxic X-irradiation as a trigger for reduction of metal ion and azide-alkyne cycloaddition on oligodeoxynucleotides. (2nd March 2022)

• Record Type: Journal Article
• Authors: Akisawa, Kento; Makanai, Hiroki; Nishihara, Tatsuya; Tanabe, Kazuhito
• Is Part Of: Tetrahedron letters. Volume 92(2022)
• Publication Date: 2022-03-02
• Subjects: CuAAC -- Oligodeoxynucleotides -- Hypoxic conditions -- Reduction of metal ion; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.153658
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A number of bioorthogonal reactions have been designed for the preparation of functional biomolecules to study their biological processes. Among them, the reaction induced by X-irradiation has attracted specific attention because it offers high biopermeability and ease of control of the reaction spatiotemporally. Herein, we demonstrate a Copper-catalysed azide-alkyne cycloaddition initiated by hypoxic X-irradiation. In the system, monovalent copper ions (Cu(I)) were generated by the radiolytic reduction of Cu(II), and the resulting metal ion accelerated the coupling between azide and acetylene molecules. We also found that the present reaction could be applied to the modification of oligodeoxynucleotides bearing acetylene unit even in shielded reaction environments by pork meat.