Here we report dual reactivity of diene-modified duplex DNA containing 5-(1,3-butadienyl)-2′-deoxyuridine “BDdU”. Normal-electron demand [4 + 2] cycloaddition proceeded upon addition of a maleimide, whereas inverse-electron demand [2 + 4] cycloaddition occurred upon addition of a tetrazine to give a novel, photoswitchable product.
![Graphical abstract: [4 + 2] and [2 + 4] cycloaddition reactions on single- and double-stranded DNA: a dual-reactive nucleoside](/en/Image/Get?imageInfo.ImageType=GA&imageInfo.ImageIdentifier.ManuscriptID=D2CB00062H&imageInfo.ImageIdentifier.Year=2022)
A. Bujalska, K. Basran and N. W. Luedtke, RSC Chem. Biol., 2022, 3, 698 DOI: 10.1039/D2CB00062H
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