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

@article{citeulike:5978353, 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 (Φ355 = 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.}, author = {Poloukhtine, Andrei A. and Mbua, Ngalle E. and Wolfert, Margreet A. and Boons, Geert-Jan and Popik, Vladimir V.}, citeulike-article-id = {5978353}, citeulike-linkout-0 = {http://dx.doi.org/10.1021/ja9054096}, citeulike-linkout-1 = {http://pubs.acs.org/doi/abs/10.1021/ja9054096}, doi = {10.1021/ja9054096}, journal = {Journal of the American Chemical Society}, keywords = {bioconjugation, click-chemistry, photochemistry}, number = {0}, posted-at = {2009-10-21 03:50:36}, priority = {2}, title = {Selective Labeling of Living Cells by a Photo-Triggered Click Reaction}, url = {http://dx.doi.org/10.1021/ja9054096}, volume = {0}, year = {0000} }

TY - JOUR ID - citeulike:5978353 L3 - citeulike-article-id:5978353 N2 - 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 (Φ355 = 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. IS - 0 JF - Journal of the American Chemical Society TI - Selective Labeling of Living Cells by a Photo-Triggered Click Reaction VL - 0 KW - bioconjugation KW - click-chemistry KW - photochemistry AU - Poloukhtine, Andrei AU - Mbua, Ngalle AU - Wolfert, Margreet AU - Boons, Geert-Jan AU - Popik, Vladimir PY - 2000/// UR - http://dx.doi.org/10.1021/ja9054096 ER -