Simple synthesis of 1,3-cyclopentanedione derived probes for labeling sulfenic acid proteins

Chem Commun (Camb). 2011 Aug 28;47(32):9203-5. doi: 10.1039/c1cc12127h. Epub 2011 Jul 8.

Abstract

Facile, two-step synthesis and kinetic characterization of new chemical probes for selective labeling of sulfenic acid (-SOH) in proteins are presented. The synthesis route relies on the simple and highly efficient Michael addition of thiol containing tags or linkers to 4-cyclopentene-1,3-dione, the unsaturated derivative of 1,3-cyclopentanedione.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Cyclopentanes / chemical synthesis*
  • Cyclopentanes / chemistry
  • Mice
  • NIH 3T3 Cells
  • Proteins / chemistry*
  • Proteins / isolation & purification
  • Staining and Labeling / methods
  • Sulfenic Acids / chemistry*
  • Sulfenic Acids / isolation & purification
  • Sulfhydryl Compounds / chemical synthesis
  • Sulfhydryl Compounds / chemistry

Substances

  • Cyclopentanes
  • Proteins
  • Sulfenic Acids
  • Sulfhydryl Compounds
  • 4-cyclopentene-1,3-dione