Fast alkene functionalization in vivo by Photoclick chemistry: HOMO lifting of nitrile imine dipoles.
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.
Wang
Yizhong
Y
Department of Chemistry, State University of New York at Buffalo, Buffalo, NY 14260, USA.
Song
Wenjiao
W
Hu
Wen J
WJ
Lin
Qing
Q
D000475:Alkenes / Q000032:analysis* / Q000737:chemistry; D003500:Cyclization; D004926:Escherichia coli / Q000166:cytology* / Q000235:genetics; D029968:Escherichia coli Proteins / Q000032:analysis* / Q000737:chemistry / Q000235:genetics; D005456:Fluorescent Dyes / Q000032:analysis* / Q000737:chemistry; D007097:Imines / Q000032:analysis / Q000737:chemistry; D007700:Kinetics; D009570:Nitriles / Q000032:analysis / Q000737:chemistry; D010777:Photochemistry; D011994:Recombinant Proteins / Q000032:analysis / Q000737:chemistry / Q000235:genetics; D013777:Tetrazoles / Q000032:analysis* / Q000737:chemistry
D000475:Alkenes; D029968:Escherichia coli Proteins; D005456:Fluorescent Dyes; D007097:Imines; D009570:Nitriles; D011994:Recombinant Proteins; D013777:Tetrazoles; C045574:1H-tetrazole