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

Org Lett. 2010 Sep 17;12(18):4208-11. doi: 10.1021/ol101863s.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Disulfides / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Phosphines / chemistry
  • S-Nitrosothiols / chemistry*

Substances

  • Disulfides
  • Phosphines
  • S-Nitrosothiols
  • phosphine