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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

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

Wang Yizhong Y Song Wenjiao W Hu Wen J WJ Lin Qing Q

Angewandte Chemie (International ed. in English) 20090101 29

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. ...[more]

PMID: 19544336

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