Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction
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 CD3CN/D2O....
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Published in | Angewandte Chemie International Edition Vol. 56; no. 40; pp. 12117 - 12121 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
WEINHEIM
Wiley
25.09.2017
Wiley Subscription Services, Inc |
Edition | International ed. in English |
Subjects | |
Online Access | Get full text |
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Summary: | 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 CD3CN/D2O. 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.
Better, faster, stronger: Perfluoroaryl azides (PFAAs) react with aryl phosphines in a fast Staudinger reaction under ambient conditions to yield kinetically stable iminophosphorane products. This PFAA Staudinger reaction proved to be an excellent bioorthogonal reaction and was successfully applied to cell‐surface labeling. |
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Bibliography: | NIH RePORTER ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1433-7851 1521-3773 1521-3773 |
DOI: | 10.1002/anie.201705346 |