Work

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

Year: 2009

Type: article

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.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja9054096

Authors: Andrei A. Poloukhtine, Ngalle Eric Mbua, Margreet A. Wolfert, Geert-Jan Boons, Vladimir V. Popik

Institution: University of Georgia

Language: English

Topic: Click Chemistry and Applications

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Cancer Institute, National Institute of General Medical Sciences

Awards: A Fully Synthetic Carbohydrate-based Cancer Vaccine, Synthetic Oligosaccharides for Probing Infection and Innate Immunity