Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction
Publication type: Journal Article
Publication date: 2017-09-01
scimago Q1
wos Q1
SJR: 5.550
CiteScore: 27.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
28796447
General Chemistry
Catalysis
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.
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86
Total citations:
86
Citations from 2024:
18
(20.93%)
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GOST
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Sundhoro M. et al. Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction // Angewandte Chemie - International Edition. 2017. Vol. 56. No. 40. pp. 12117-12121.
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Sundhoro M., Jeon S., Park J., Ramström O., Yan M. Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction // Angewandte Chemie - International Edition. 2017. Vol. 56. No. 40. pp. 12117-12121.
Cite this
RIS
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TY - JOUR
DO - 10.1002/anie.201705346
UR - https://doi.org/10.1002/anie.201705346
TI - Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction
T2 - Angewandte Chemie - International Edition
AU - Sundhoro, Madanodaya
AU - Jeon, Seaho
AU - Park, Jaehyeung
AU - Ramström, Olof
AU - Yan, Mingdi
PY - 2017
DA - 2017/09/01
PB - Wiley
SP - 12117-12121
IS - 40
VL - 56
PMID - 28796447
SN - 1433-7851
SN - 1521-3773
ER -
Cite this
BibTex (up to 50 authors)
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@article{2017_Sundhoro,
author = {Madanodaya Sundhoro and Seaho Jeon and Jaehyeung Park and Olof Ramström and Mingdi Yan},
title = {Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction},
journal = {Angewandte Chemie - International Edition},
year = {2017},
volume = {56},
publisher = {Wiley},
month = {sep},
url = {https://doi.org/10.1002/anie.201705346},
number = {40},
pages = {12117--12121},
doi = {10.1002/anie.201705346}
}
Cite this
MLA
Copy
Sundhoro, Madanodaya, et al. “Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction.” Angewandte Chemie - International Edition, vol. 56, no. 40, Sep. 2017, pp. 12117-12121. https://doi.org/10.1002/anie.201705346.