Multifluorinated Aryl Azides for the Development of Improved H2S Probes, and Fast Strain‐promoted Azide‐Alkyne Cycloaddition and Staudinger Reactions

The development of advanced bioorthogonal reactions for detection and labeling of biomolecules is significant in chemical biology. Recently, researchers have found that multifluorinated aryl azides hold great potential for the development of improved bioorthogonal reactions. The fluorine atom can be...

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Bibliographic Details
Published in:Chemistry, an Asian journal an Asian journal, 2020-05, Vol.15 (9), p.1420-1429
Main Authors: Kang, Xueying, Cai, Xuekang, Yi, Long, Xi, Zhen
Format: Article
Language:English
Subjects:
Alkynes
Aromatic compounds
Biomolecules
Chemical reactions
Chemistry
Cycloaddition
Electronegativity
Fluorescent indicators
Fluorinated aryl azide
Fluorine
Hydrogen sulfide
Kinetics
SPAAC
Staudinger reaction
Steric hindrance
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Summary:The development of advanced bioorthogonal reactions for detection and labeling of biomolecules is significant in chemical biology. Recently, researchers have found that multifluorinated aryl azides hold great potential for the development of improved bioorthogonal reactions. The fluorine atom can be a perfect substituent group because of its properties of excellent electronegativity and small steric hindrance. In this Minireview, we discuss recent developments of improved hydrogen sulfide (H2S) fluorescence probes, fast strain‐promoted azide‐alkyne cycloaddition (SPAAC) and nonhydrolysis Staudinger reactions based on the use of multifluorinated aryl azides. Additionally, kinetic studies and biological applications of these reactions are also presented. Multifluorinated aryl azides for fast‐response H2S fluorescence probes as well as advanced SPAAC and Staudinger reactions are summarized. The nonhydrolysis Staudinger reaction based on the tetrafluorinated aryl azide can be efficient enough (>51 M−1s−1) for biolabeling of proteins and nucleic acids.
ISSN:1861-4728
1861-471X
DOI:10.1002/asia.202000005