Electrophilic sulfhydration of 8-nitro-cGMP involves sulfane sulfur

Org Biomol Chem. 2014 Aug 7;12(29):5360-4. doi: 10.1039/c4ob00868e.

Abstract

The formation of 8-SH-cGMP from the reaction between hydrogen sulfide and 8-nitro-guanosine-3',5'-cyclic monophosphate in the presence of thiols does not take place by nucleophilic attack of the hydrosulfide anion, as previously proposed, but first involves the formation of reactive species containing sulfane sulfur, like persulfides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anaerobiosis
  • Cyclic GMP / analogs & derivatives*
  • Cyclic GMP / chemistry
  • Electron Spin Resonance Spectroscopy
  • Electrons*
  • Hydrogen Sulfide / chemistry
  • Spectrophotometry, Ultraviolet
  • Sulfhydryl Compounds / chemistry
  • Sulfur / chemistry*

Substances

  • 8-nitroguanosine 3',5'-cyclic monophosphate
  • Sulfhydryl Compounds
  • Sulfur
  • Cyclic GMP
  • Hydrogen Sulfide