Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 40, Pages 12117-12121Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201705346
Keywords
bioconjugation; bioorthogonal reactions; metabolic labelling; perfluoroaryl azides; Staudinger reaction
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Funding
- National Institutes of Health [R01GM080295, R21AI109896]
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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 18m(-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.
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