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Fast Alkene Functionalization In Vivo by Photoclick Chemistry: HOMO Lifting of Nitrile Imine Dipoles
Author(s) -
Wang Yizhong,
Song Wenjiao,
Hu Wen J.,
Lin Qing
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200901220
Subject(s) - nitrile , alkene , chemistry , tetrazole , surface modification , cycloaddition , imine , substituent , 1,3 dipolar cycloaddition , photochemistry , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
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.