A significant expansion of an existing library of fluorescein ester derivatives was accomplished, adding more depth and breadth to the existing library. These fluorogenic esters are particularly useful in probing enzymatic esterase activity for substrate specificity. Using a divergent synthetic pathway from bis(chloromethyl) fluorescein ether starting material and various carboxylic acids, 12 new esters containing various functionality, branching, and chain lengths have been successfully synthesized and characterized by 1H-NMR, 13C-NMR, and HRMS. Several of the new derivatives were used in the biochemical assay of the FTT258 enzyme from the Francisella tularensis bacterium. The results demonstrated a strong preference for straight chain alkyl derivatives over newly synthesized alpha branched and chlorovinyl-substituted analogs.

Synthesis of fluorogenic esters for bacterial esterase characterization

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.