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Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction.

Sundhoro, Madanodaya; Jeon, Seaho; Park, Jaehyeung; Ramström, Olof; Yan, Mingdi.
Angew Chem Int Ed Engl; 56(40): 12117-12121, 2017 Sep 25.
Artigo em Inglês | MEDLINE | ID: mdl-28796447
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 CD3 CN/D2 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.
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