The chemical modification of amino acids is an important tool for studying protein interactions. Tyrosine has shown to be an attractive target for chemical modification, however further development of chemical tools is needed. Aryl diazonium ions label tyrosine residues in a selective and fast manner, but the harshly acidic conditions required for aryl diazonium ion generation limits experimentation to <i>in vitro</i> studies. Our lab has developed a mild method to generate aryl diazonium ions through the use of molecules called triazabutadiene. Triazabutadienes contain a π-conjugated nitrogen-rich system, and in the presence of mildly acidic conditions (such as physiological pH) the molecule becomes protonated and releases an aryl diazonium ion. The addition of a self-immolative protecting group to triazabutadienes allows further stability and precise release of the aryl diazonium ion. We aspire to use a triggering event to unlock triazabutadienes for aryl diazonium ion generation.<br/>

Using protected triazabutadienes for aryl diazonium ion generation

255th National Meeting (2018)

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