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

Hide authors affiliations Show authors affiliations: 3 affiliations

State Key Laboratory of Elemento-Organic Chemistry and Department of Chemical Biology, National Pesticide Engineering Research Center (Tianjin); Collaborative Innovation Center of Chemical Science and Engineering (Tianjin); College of Chemistry; Nankai University; China

Nankai University

Collaborative Innovation Center of Chemical Science and Engineering Tianjin

State Key Laboratory of Organic-Inorganic Composites; Beijing University of Chemical Technology (BUCT); Beijing 100029 China |

Department of Nuclear Medicine; Peking University First Hospital; Beijing 100034 China |

Publication type: Journal Article

Publication date: 2018-06-21

Wiley

Chemistry - An Asian Journal

scimago Q2

wos Q2

SJR: 0.751

CiteScore: 5.9

Impact factor: 3.3

ISSN: 18614728, 1861471X

DOI: 10.1002/asia.201800503

Copy DOI

PubMed ID: 29714052

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.

Found

1 citation

Osipov Sergey

DSc in Chemistry

138 publications, 2 751 citations, 3 reviews

h-index: 29

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

1 citation

Shchegolkov Evgeny

70 publications, 927 citations, 57 reviews

h-index: 16

Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Research interests

Organic synthesis

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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) Copy

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.

RIS |

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RIS Copy

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 - Cheng, Longhuai

AU - Gao, Yasi

AU - Cai, Xuekang

AU - Yang, Xing

AU - Yi, Long

AU - Xi, Zhen

PY - 2018

DA - 2018/06/21

PB - Wiley

SP - 1791-1796

IS - 14

VL - 13

PMID - 29714052

SN - 1861-4728

SN - 1861-471X

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2018_Xie,

author = {Yonghui Xie and Longhuai Cheng and Yasi Gao and Xuekang Cai and Xing Yang and Long Yi 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}

}

MLA

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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.

Publisher

Wiley

Journal

Chemistry - An Asian Journal

scimago Q2

wos Q2

SJR

0.751

CiteScore

5.9

Impact factor

3.3

ISSN

18614728 (Print)

1861471X (Electronic)