Tetrahedron letters2022,Vol.924.DOI:10.1016/j.tetlet.2022.153658

Hypoxic X-irradiation as a trigger for reduction of metal ion and azide-alkyne cycloaddition on oligodeoxynucleotides

Akisawa, Kento Makanai, Hiroki Nishihara, Tatsuya Tanabe, Kazuhito
Tetrahedron letters2022,Vol.924.DOI:10.1016/j.tetlet.2022.153658

Hypoxic X-irradiation as a trigger for reduction of metal ion and azide-alkyne cycloaddition on oligodeoxynucleotides

Akisawa, Kento 1Makanai, Hiroki 1Nishihara, Tatsuya 1Tanabe, Kazuhito1
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作者信息

  • 1. Aoyama Gakuin Univ
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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. (c) 2022 Elsevier Ltd. All rights reserved.

Key words

CuAAC/Oligodeoxynucleotides/Hypoxic conditions/Reduction of metal ion/ONE-ELECTRON REDUCTION/ACTIVATION

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出版年

2022
Tetrahedron letters

Tetrahedron letters

CCR
ISSN:0040-4039
参考文献量19
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