Synthesis of Chemical Probes to Map Sulfenic Acid Modifications on Proteins

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• 作者：Leslie B. Poole ; Bu-Bing Zeng ; Sarah A. Knaggs ; Mamudu Yakubu ; and S. Bruce King
• 刊名：Bioconjugate Chemistry
• 出版年：2005
• 出版时间：November 2005
• 年：2005
• 卷：16
• 期：6
• 页码：1624 - 1628
• 全文大小：96K
• 年卷期：v.16,no.6(November 2005)
• ISSN：1520-4812

文摘

Cysteine sulfenic acids in proteins can be identified by their ability to form adducts with dimedone,but this reagent imparts no spectral or affinity tag for subsequent analyses of such tagged proteins.Given its similar reactivity toward cysteine sulfenic acids, 1,3-cyclohexadione was syntheticallymodified to an alcohol derivative and linked to fluorophores based on isatoic acid and 7-methoxycoumarin. The resulting compounds retain full reactivity and specificity toward cysteine sulfenic acidsin proteins, allowing for incorporation of the fluorescent label into the protein and "tagging" it basedon its sulfenic acid redox state. Control experiments using dimedone further show the specificity ofthe reaction of 1,3-diones with protein sulfenic acids in aqueous media. These new compounds providethe basis for an improved method for the detection of protein sulfenic acids.