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Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction
Author(s) -
Sundhoro Madanodaya,
Jeon Seaho,
Park Jaehyeung,
Ramström Olof,
Yan Mingdi
Publication year - 2017
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.201705346
Subject(s) - staudinger reaction , azide , chemistry , phosphonium , ylide , hydrolysis , conjugated system , cycloaddition , bioorthogonal chemistry , combinatorial chemistry , organic chemistry , medicinal chemistry , click chemistry , polymer , catalysis
We report a fast Staudinger reaction between perfluoroaryl azides (PFAAs) and aryl phosphines, which occurs readily under ambient conditions. A rate constant as high as 18 m −1 s −1 was obtained between methyl 4‐azido‐2,3,5,6‐tetrafluorobenzoate and methyl 2‐(diphenylphosphanyl)benzoate in CD 3 CN/D 2 O. Furthermore, the iminophosphorane product was stable toward hydrolysis and aza‐phosphonium ylide reactions. This PFAA Staudinger reaction proved to be an excellent bioothorgonal reaction. PFAA‐derivatized mannosamine and galactosamine were successfully transformed into cell‐surface glycans and efficiently labeled with phosphine‐derivatized fluorophore‐conjugated bovine serum albumin.