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Bioorg Med Chem Lett. 2009 Jan 15;19(2):356-9. doi: 10.1016/j.bmcl.2008.11.073. Epub 2008 Nov 24.

Facile synthesis and biological evaluation of a cell-permeable probe to detect redox-regulated proteins.

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Life Sciences Institute, University of Michigan, 210 Washtenaw Ave. #4401, Ann Arbor, MI 48109-2216, USA.


We have developed an improved synthesis for the cell-permeable, sulfenic acid probe DAz-1. Using DAz-1, we detect sulfenic acid modifications in the cell-cycle regulatory phosphatase Cdc25A. In addition, we show that DAz-1 has superior potency in cells compared to a biotinylated derivative. Collectively, these findings set the stage for the development of activity-based inhibitors of Cdc25 cell-cycle phosphatases, which are sensitive to the redox state of the active-site cysteine and demonstrate the advantage of bioorthogonal conjugation methods to detect protein sulfenic acids in cells.

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