Improved Photoinduced Fluorogenic Alkene-Tetrazole Reaction for Protein Labeling.

ABSTRACT: The 1,3-dipolar cycloaddition reaction between an alkene and a tetrazole represents one elegant and rare example of fluorophore-forming bioorthogonal chemistry. This is an attractive reaction for imaging applications in live cells that requires less intensive washing steps and/or needs spatiotemporal resolutions. In the present work, as an effort to improve the fluorogenic property of the alkene-tetrazole reaction, an aromatic alkene (styrene) was investigated as the dipolarophile. Over 30-fold improvement in quantum yield of the reaction product was achieved in aqueous solution. According to our mechanistic studies, the observed improvement is likely due to an insufficient protonation of the styrene-tetrazole reaction product. This finding provides useful guidance to the future design of

SUBMITTER: Shang X 

PROVIDER: S-EPMC5688003 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature