Fluorescent compounds based on synthetic small molecules are powerful tools for visualizing biological events. Their small size offers the advantage of minimizing the perturbation of the system being studied. Despite the advances that have been made in the construction of small molecule fluorophores, rationally designed fluorescent probes possessing varied and tuned photophysical, spectral and chemical properties are still needed. Here we report the design and synthesis of stabilized and masked variations of a borylbenzodiazonium reagent. This versatile system was used as a tool for the synthesis of fluorophores from a diverse library of electron rich aromatic small molecules in a single step under mild conditions. Because the aromatic molecules are incorporated into the core of the fluorophore, it allows for a high degree of photophysical and spectral tuning capability. The reagent was also shown to be capable of labeling tyrosine residues containing proteins and peptides under biologically relevant conditions. Since neither the reagent nor the protein is inherently florescent, this fluorogenic system does not suffer from background fluorescence. This opens the door for an in vivo labeling strategy of proteins as well as a fluorogenic crosslinker to study protein interaction. References; 1.Pflugers Arch. 2013 ;465(3):347-59 2.Chem Commun . 2007; 14;(6):559-61.

Borylbenzodiazonium reagent for library fluorophore synthesis and biological application

251st National Meeting (2016)

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