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Fast Alkene Functionalization In Vivo by Photoclick Chemistry: HOMO Lifting of Nitrile Imine Dipoles

2009; Wiley; Volume: 48; Issue: 29 Linguagem: Inglês

10.1002/anie.200901220

1521-3773

Yi‐Zhong Wang, Wenjiao Song, Wen J. Hu, Qing Lin,

Monoclonal and Polyclonal Antibodies Research

Extremely fast fluorescence labeling (<1 min) of a recombinant alkene-encoded protein in living Escherichia coli cells was observed with tetrazole 1. The electron-donating methoxy substituent raises the energy of the highest occupied molecular orbital of the nitrile-imine intermediate derived from 1. This strategy greatly accelerates the functionalization of alkenes by 1,3-dipolar cycloaddition in living systems.