Unknown

Dataset Information

0

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

altmetric image

Publications

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<sup>-1</sup>  s<sup>-1</sup> was obtained between methyl 4-azido-2,3,5,6-tetrafluorobenzoate and methyl 2-(diphenylphosphanyl)benzoate in CD<sub>3</sub> CN/D<sub>2</sub> O. Furthermore, the iminophosphorane product was stable toward hydrolysis and aza-phosphonium ylide reactions. This PFAA Staudinger reaction proved to be an  ...[more]

Similar Datasets

| S-EPMC6754110 | biostudies-literature
| S-EPMC6337264 | biostudies-literature
| S-EPMC9608709 | biostudies-literature
| S-EPMC5113785 | biostudies-literature
| S-EPMC3869290 | biostudies-literature
| S-EPMC6794642 | biostudies-literature
2024-04-15 | GSE231507 | GEO
| S-EPMC7371345 | biostudies-literature
| S-EPMC6377280 | biostudies-literature
| S-EPMC4516611 | biostudies-literature