Selective Functionalization of a Genetically Encoded Alkene-Containing Protein via “Photoclick Chemistry” in Bacterial Cells

Wenjiao Song†, Yizhong Wang†, Jun Qu‡ and Qing Lin†
Departments of Chemistry and Pharmaceutical Sciences, State University of New York at Buffalo, Buffalo, New York 14260
J. Am. Chem. Soc., 2008, 130 (30), pp 9654–9655
DOI: 10.1021/ja803598e
Publication Date (Web): July 2, 2008
Copyright © 2008 American Chemical Society
†

Department of Chemistry.

,
‡

Department of Pharmaceutical Sciences.

Abstract

Abstract Image

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 °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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History

  • Published In Issue July 30, 2008
  • Article ASAPJuly 02, 2008
  • Received: May 14, 2008

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