Multifluorinated Aryl Azides for the Development of Improved H2 S Probes, and Fast Strain-promoted Azide-Alkyne Cycloaddition and Staudinger Reactions

Abstract

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 (H₂ S) 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.

Keywords: Fluorinated aryl azide; Kinetics; SPAAC; Staudinger reaction; hydrogen sulfide.