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Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction.

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 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.

SUBMITTER: Sundhoro M

PROVIDER: S-EPMC5693246 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature

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Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction.

Sundhoro Madanodaya M Jeon Seaho S Park Jaehyeung J Ramström Olof O Yan Mingdi M

Angewandte Chemie (International ed. in English) 20170901 40

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 ...[more]

PMID: 28796447

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