Angewandte Chemie - International Edition, volume 56, issue 40, pages 12117-12121
Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction
1
Department of Chemistry; University of Massachusetts Lowell; 1 University Ave. Lowell MA 01854 USA
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Publication type: Journal Article
Publication date: 2017-09-01
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 16.6
ISSN: 14337851, 15213773
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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Citations by publishers
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5
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15
20
25
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Wiley
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1 publication, 1.37%
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1 publication, 1.37%
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5
10
15
20
25
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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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.
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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 - Jeon, Seaho
AU - Park, Jaehyeung
AU - Ramström, Olof
AU - Yan, Mingdi
AU - Sundhoro, Madanodaya
PY - 2017
DA - 2017/09/01 00:00:00
PB - Wiley
SP - 12117-12121
IS - 40
VL - 56
SN - 1433-7851
SN - 1521-3773
ER -
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@article{2017_Sundhoro,
author = {Seaho Jeon and Jaehyeung Park and Olof Ramström and Mingdi Yan and Madanodaya Sundhoro},
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}
}
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MLA
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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.