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Issue 18, 2011
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Design, synthesis and photoactivation studies of fluorous photolabels

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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.

Graphical abstract: Design, synthesis and photoactivation studies of fluorous photolabels

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Supplementary files

Article information


Submitted
12 May 2011
Accepted
13 Jun 2011
First published
13 Jun 2011

Org. Biomol. Chem., 2011,9, 6284-6292
Article type
Paper

Design, synthesis and photoactivation studies of fluorous photolabels

A. Babu Kumar, J. M. Anderson and R. Manetsch, Org. Biomol. Chem., 2011, 9, 6284
DOI: 10.1039/C1OB05748K

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