Development of a Fluorogenic Reactivity Palette for the Study of Nucleophilic Addition Reactions Based on meso-Formyl BODIPY Dyes.

ABSTRACT: We describe herein a fluorescence-based assay to characterize and report on nucleophilic addition to carbonyl moieties and highlight the advantages a fluorescence-based assay and multiplex analysis can offer. The assay relies on the fluorogenic properties of meso-formyl boron-dipyrromethene (BODIPY) dyes that become emissive following nucleophilic addition. A reactivity palette is assembled based on the increasing electrophilic character of five meso-formyl BODIPY compounds tested. We show that increasing rates of emission enhancement correlate with the decreasing electrophilic character of BODIPY dyes in the presence of an acid catalyst and a nucleophile. These results are consistent with the rate-limiting step involving activation of the electrophile. Increasing product for

SUBMITTER: Greene LE 

PROVIDER: S-EPMC6645663 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature