Chemistry - An Asian Journal, volume 13, issue 14, pages 1791-1796
Tetrafluorination of Aromatic Azide Yields a Highly Efficient Staudinger Reaction: Kinetics and Biolabeling
Yonghui Xie
1
,
Longhuai Cheng
1
,
Yasi Gao
2
,
Xuekang Cai
2, 3
,
Xing Yang
3
,
Long Yi
2
,
Zhen Xi
1
Publication type: Journal Article
Publication date: 2018-06-21
Journal:
Chemistry - An Asian Journal
Quartile SCImago
Q1
Quartile WOS
Q2
SJR: 0.846
CiteScore: 7.0
Impact factor: 3.5
ISSN: 18614728, 1861471X
General Chemistry
Organic Chemistry
Biochemistry
Abstract
The development of highly efficient bioorthogonal reactions is of paramount importance for the research fields of biomaterials and chemical biology. We found that the o,o'-difluorinated aromatic azide was able to react with triphenylphosphine to produce water-stable phosphanimine. To further improve the efficiency of this kind of nonhydrolysis Staudinger reaction, a tetrafluorinated aromatic azide was employed to develop a faster nonhydrolysis Staudinger reaction with a rate of up to 51 m-1 s-1 , as revealed by high-performance liquid chromatography (HPLC) analysis and fluorescence kinetics. As a proof-of-concept study, the highly efficient Staudinger reaction was successfully used for chemoselective fluorescence labeling of proteins and nucleic acids (DNA and RNA) as well as for protein polyethyleneglycol (PEG)ylation. We believe that this bioorthogonal reaction can provide a broadly useful tool for various bioconjugations.
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GOST
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Xie Y. et al. Tetrafluorination of Aromatic Azide Yields a Highly Efficient Staudinger Reaction: Kinetics and Biolabeling // Chemistry - An Asian Journal. 2018. Vol. 13. No. 14. pp. 1791-1796.
GOST all authors (up to 50)
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Xie Y., Cheng L., Gao Y., Cai X., Yang X., Yi L., Xi Z. Tetrafluorination of Aromatic Azide Yields a Highly Efficient Staudinger Reaction: Kinetics and Biolabeling // Chemistry - An Asian Journal. 2018. Vol. 13. No. 14. pp. 1791-1796.
Cite this
RIS
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TY - JOUR
DO - 10.1002/asia.201800503
UR - https://doi.org/10.1002/asia.201800503
TI - Tetrafluorination of Aromatic Azide Yields a Highly Efficient Staudinger Reaction: Kinetics and Biolabeling
T2 - Chemistry - An Asian Journal
AU - Xie, Yonghui
AU - Gao, Yasi
AU - Cai, Xuekang
AU - Yi, Long
AU - Cheng, Longhuai
AU - Yang, Xing
AU - Xi, Zhen
PY - 2018
DA - 2018/06/21
PB - Wiley
SP - 1791-1796
IS - 14
VL - 13
SN - 1861-4728
SN - 1861-471X
ER -
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@article{2018_Xie,
author = {Yonghui Xie and Yasi Gao and Xuekang Cai and Long Yi and Longhuai Cheng and Xing Yang and Zhen Xi},
title = {Tetrafluorination of Aromatic Azide Yields a Highly Efficient Staudinger Reaction: Kinetics and Biolabeling},
journal = {Chemistry - An Asian Journal},
year = {2018},
volume = {13},
publisher = {Wiley},
month = {jun},
url = {https://doi.org/10.1002/asia.201800503},
number = {14},
pages = {1791--1796},
doi = {10.1002/asia.201800503}
}
Cite this
MLA
Copy
Xie, Yonghui, et al. “Tetrafluorination of Aromatic Azide Yields a Highly Efficient Staudinger Reaction: Kinetics and Biolabeling.” Chemistry - An Asian Journal, vol. 13, no. 14, Jun. 2018, pp. 1791-1796. https://doi.org/10.1002/asia.201800503.