SYNTHESIS OF NOVEL TRIAZINES, CHEMICAL PROPERTIES AND THEIR APPLICATIONS IN BIOCHEMISTRY

Abstract

Aryl diazonium ions serve as a powerful tool in bioconjugation, protein functionalization, and numerous applications present in biochemical literature dating over a century. The synthesis and utility of these reagents is typically restricted to in vitro environments due to the biologically incompatible nature of their generation, as well as their stability. As a result, protection mechanisms, like triazabutadiene scaffolds have been synthesized and further functionalized to release aryl diazonium ions selectively in vivo. Here, we detail the generation and study of novel triazines for use in protecting aryl diazonium ions, synthesized by addition of morpholine and piperazine, and capable of initiated diazonium delivery via UV irradiation. One of our goals is to determine how protecting one of the piperazine amines affects the nucleophilicity of the remaining amine group of piperazine.