Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 19, Issue 2, Pages 356-359Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2008.11.073
Keywords
Redox regulation; Cysteine oxidation; Sulfenic acids; Tyrosine phosphatase; Chemical probes; Staudinger ligation; Click chemistry
Categories
Funding
- Life Sciences Institute
- Leukemia & Lymphoma Society [3100-07]
- American Heart Association Scientist Development [0835419N]
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We have developed an improved synthesis for the cell-permeable, sulfenic acid probe DAz-1. Using DAz-1, we detect sulfenic acid modi. cations 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. (C) 2008 Elsevier Ltd. All rights reserved.
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