Optimization of the azobenzene scaffold for reductive cleavage by dithionite; development of an azobenzene cleavable linker for proteomic applications

G Leriche, G Budin, L Brino…

Index: Leriche, Geoffray; Budin, Ghyslain; Brino, Laurent; Wagner, Alain European Journal of Organic Chemistry, 2010 , # 23 p. 4360 - 4364

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Citation Number: 25

Abstract

Abstract 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-O-alkyl-resorcinol as the electron-rich arene. Based on this 2-(2′-alkoxy-4′- ...