Fast alkene functionalization in vivo by Photoclick chemistry: HOMO lifting of nitrile imine dipoles.

ABSTRACT: 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.

SUBMITTER: Wang Y 

PROVIDER: S-EPMC2763439 | biostudies-literature | 2009

REPOSITORIES: biostudies-literature