Oxidation of 8-thioguanosine gives redox-responsive hydrogels and reveals intermediates in a desulfurization pathway

Chem Commun (Camb). 2020 Jun 25;56(51):6981-6984. doi: 10.1039/d0cc02926b.

Abstract

A disulfide made by oxidation of 8-thioguanosine is a supergelator. The hydrogels are redox-responsive, as they disassemble upon either reduction or oxidation of the S-S bond. We also identified this disulfide, and 2 other compounds, as intermediates in oxidative desulfurization of 8-thioG to guanosine.

MeSH terms

  • Density Functional Theory
  • Disulfides / chemistry*
  • Guanosine / analogs & derivatives*
  • Guanosine / chemistry
  • Hydrogels / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Thionucleosides / chemistry*

Substances

  • Disulfides
  • Hydrogels
  • Thionucleosides
  • Guanosine
  • 8-thioguanosine