20032-71-7Relevant articles and documents
Optimization of the azobenzene scaffold for reductive cleavage by dithionite; development of an azobenzene cleavable linker for proteomic applications
Leriche, Geoffray,Budin, Ghyslain,Brino, Laurent,Wagner, Alain
experimental part, p. 4360 - 4364 (2010/09/20)
In this paper we conducted an extensive reactivity study to determine the key structural features that favour the dithionite-triggered reductive cleavage of the azo-arene group. Our stepwise investigation allowed identification of a highly reactive azo-arene structure 25 bearing a carboxylic acid, at the ortho position of the electron-poor arene and an ortho-Oalkyl-resorcinol as the electron-rich arene. Based on this 2(2′-alkoxy-4′-hydroxyphenylazo) benzoic acid (HAZA) scaffold, the orthogonally protected difunctional azo-arene cleavable linker 26 was designed and synthesized. Selective linker deprotection and derivatization was performed by introducing an alkyne reactive group and a biotin affinity tag. This optimized azo-arene cleavable linker led to a total cleavage in less than 10 s with only 1 mM dithionite. Similar results were obtained in biological media.
