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Chemoselective ratiometric imaging of protein S-sulfenylation†
Christopher T. M. B. Tom,John E. Crellin,Hashim F. Motiwala,Matthew B. Stone,Dahvid Davda,William Walker,Yu-Hsuan Kuo,Jeannie L. Hernandez,Kristin J. Labby,Lyanne Gomez-Rodriguez,Paul M. Jenkins,Sarah L. Veatch,Brent R. Martin
Chemical Communications Pub Date : 06/07/2017 00:00:00 , DOI:10.1039/C7CC02285A
Abstract

Here we report a ratiometric fluorescent probe for chemoselective conjugation to sulfenic acids in living cells. Our approach couples an α-fluoro-substituted dimedone to an aminonaphthalene fluorophore (F-DiNap), which upon sulfenic acid conjugation is locked as the 1,3-diketone, changing the fluorophore excitation. F-DiNap reacts with S-sulfenylated proteins at equivalent rates to current probes, but the α-fluorine substitution blocks side-reactions with biological aldehydes.

Graphical abstract: Chemoselective ratiometric imaging of protein S-sulfenylation
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