Reductive ligation mediated one-step disulfide formation of S -nitrosothiols

Jiming Zhang, Sheng Li, Dehui Zhang, Hua Wang, A. Richard Whorton, Ming Xian

Research output: Contribution to journalArticle

45 Scopus citations

Abstract

A one-step reductive ligation mediated disulfide formation of S-nitrosothiols was developed. This reaction involves the reaction of the S-nitroso group with phosphine-thioesters to form sulfenamide and thiolate intermediates, which then undergo a fast intermolecular disulfide formation to form stable conjugates. This reaction can be used to design new biosensors of S-nitrosated proteins.

Original languageEnglish (US)
Pages (from-to)4208-4211
Number of pages4
JournalOrganic Letters
Volume12
Issue number18
DOIs
Publication statusPublished - Sep 17 2010

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Zhang, J., Li, S., Zhang, D., Wang, H., Whorton, A. R., & Xian, M. (2010). Reductive ligation mediated one-step disulfide formation of S -nitrosothiols. Organic Letters, 12(18), 4208-4211. https://doi.org/10.1021/ol101863s