Tetrafluorination of Aromatic Azide Yields a Highly Efficient Staudinger Reaction: Kinetics and Biolabeling

Yonghui Xie, Longhuai Cheng, Yasi Gao, Xuekang Cai, Xing Yang, Long Yi, Zhen Xi

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
Pages (from-to)1791-1796
Number of pages6
JournalChemistry - An Asian Journal
Volume13
Issue number14
DOIs
StatePublished - Jul 16 2018
Externally publishedYes

Keywords

  • azides
  • biolabeling
  • kinetics
  • RNA
  • Staudinger reaction

ASJC Scopus subject areas

  • Chemistry(all)

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