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

44 Citations (Scopus)

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
StatePublished - Sep 17 2010
Externally publishedYes

Fingerprint

S-Nitrosothiols
phosphine
disulfides
Disulfides
Ligation
Protein S
Biosensing Techniques
Biosensors
bioinstrumentation
phosphines
proteins
Proteins

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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

Reductive ligation mediated one-step disulfide formation of S -nitrosothiols. / Zhang, Jiming; Li, Sheng; Zhang, Dehui; Wang, Hua; Whorton, A. Richard; Xian, Ming.

In: Organic Letters, Vol. 12, No. 18, 17.09.2010, p. 4208-4211.

Research output: Contribution to journalArticle

Zhang, J, Li, S, Zhang, D, Wang, H, Whorton, AR & Xian, M 2010, 'Reductive ligation mediated one-step disulfide formation of S -nitrosothiols', Organic Letters, vol. 12, no. 18, pp. 4208-4211. https://doi.org/10.1021/ol101863s
Zhang J, Li S, Zhang D, Wang H, Whorton AR, Xian M. Reductive ligation mediated one-step disulfide formation of S -nitrosothiols. Organic Letters. 2010 Sep 17;12(18):4208-4211. https://doi.org/10.1021/ol101863s
Zhang, Jiming ; Li, Sheng ; Zhang, Dehui ; Wang, Hua ; Whorton, A. Richard ; Xian, Ming. / Reductive ligation mediated one-step disulfide formation of S -nitrosothiols. In: Organic Letters. 2010 ; Vol. 12, No. 18. pp. 4208-4211.
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