Design, synthesis and photoactivation studies of fluorous photolabels

Abstract

Two fluorous diazirine photolabels were designed, synthesized and subjected to photoactivation studies. The photoactivation studies revealed an unexpected photoreaction when the fluorous tag was directly connected to the diazirine ring, leading to the formation of a fluorous alkene. The more efficient photolabel of the two was identified as a flexible precursor for target specific photoaffinity labels for fluorous proteomics by adding appropriate ligands depending on the target protein subset. As a proof of feasibility, mannose residues were added to the photolabel making it a potential photoaffinity label to tag proteins that bind mannose.