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J Am Chem Soc. 2008 Jul 30;130(30):9654-5. doi: 10.1021/ja803598e. Epub 2008 Jul 2.

Selective functionalization of a genetically encoded alkene-containing protein via "photoclick chemistry" in bacterial cells.

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Department of Chemistry, State University of New York at Buffalo, Buffalo, New York 14260, USA.


We report a tetrazole-based, photoclick chemistry that can be employed to selectively functionalize an alkene genetically encoded in a protein inside E. coli cells. The reaction involved the treatment of E. coli cells with cell-permeable tetrazoles followed by a brief photo irradiation at 302 nm (4 min) and an overnight incubation at 4 degrees C. This in vivo alkene functionalization procedure was simple, straightforward, and nontoxic to E. coli cells. Additionally, fluorescent adducts were formed, facilitating the monitoring of the reaction in vivo. This reaction should offer a new tool for the study of alkene-containing proteins in living systems.

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