Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction

Madanodaya Sundhoro, Seaho Jeon, Jaehyeung Park, Olof Ramström, Mingdi Yan

Research output: Contribution to journalArticlepeer-review

74 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)12117-12121
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number40
DOIs
StatePublished - 25 Sep 2017

Keywords

  • bioconjugation
  • bioorthogonal reactions
  • metabolic labelling
  • perfluoroaryl azides
  • Staudinger reaction

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