Facile Conversion of Cysteine and Alkyl Cysteines to Dehydroalanine on Protein Surfaces: Versatile and Switchable Access to Functionalized Proteins

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• 作者：Gonç ; alo J. L. Bernardes ; Justin M. Chalker ; James C. Errey ; Benjamin G. Davis
• 刊名：Journal of the American Chemical Society
• 出版年：2008
• 出版时间：April 16, 2008
• 年：2008
• 卷：130
• 期：15
• 页码：5052 - 5053
• 全文大小：661K
• 年卷期：v.130,no.15(April 16, 2008)
• ISSN：1520-5126

文摘

An efficient and robust oxidative elimination of cysteine to dehydroalanine has been discovered. The reaction is induced by O-mesitylenesulfonylhydroxylamine (MSH) and is compatible with methionine. The key elimination has been executed on protein surfaces and allows ready access to different post-translationally modified proteins through conjugate addition of sulfur nucleophiles to dehydroalanine. Treatment of the resulting thioether with MSH results in regeneration of dehydroalanine, allowing a ȁc;functional switch” by subsequent addition of a different thiol.