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American Chemical Society, Journal of the American Chemical Society, 43(131), p. 15769-15776, 2009

DOI: 10.1021/ja9054096

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Selective Labeling of Living Cells by a Photo-Triggered Click Reaction

Journal article published in 2009 by Andrei A. Poloukhtine, Ngalle Eric Mbua, Margreet A. Wolfert ORCID, Geert-Jan Boons ORCID, Vladimir V. Popik
This paper is available in a repository.
This paper is available in a repository.

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Abstract

Phototriggering of the metal-free azide to acetylene cycloaddition reaction was achieved by masking the triple bond of dibenzocyclooctynes as cyclopropenone. Such masked cyclooctynes do not react with azides in the dark. Irradiation of cyclopropenones results in the efficient (Phi(355) = 0.33) and clean regeneration of the corresponding dibenzocyclooctynes, which then undergo facile catalyst-free cycloadditions with azides to give corresponding triazoles under ambient conditions. In situ light activation of a cyclopropenone linked to biotin made it possible to label living cells expressing glycoproteins containing N-azidoacetyl-sialic acid. The cyclopropenone-based phototriggered click chemistry offers exciting opportunities to label living organisms in a temporally and spatially controlled manner and may facilitate the preparation of microarrays.