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Selective labeling of living cells by a photo-triggered click reaction.

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.

SUBMITTER: Poloukhtine AA

PROVIDER: S-EPMC2776736 | biostudies-literature | 2009 Nov

REPOSITORIES: biostudies-literature

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Selective labeling of living cells by a photo-triggered click reaction.

Poloukhtine Andrei A AA Mbua Ngalle Eric NE Wolfert Margreet A MA Boons Geert-Jan GJ Popik Vladimir V VV

Journal of the American Chemical Society 20091101 43

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 a ...[more]

PMID: 19860481

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