Facile dimethylarsenic exchange and pyramidal inversion in its cysteine and glutathione adducts

Org Biomol Chem. 2013 Apr 28;11(16):2578-81. doi: 10.1039/c3ob40268a.

Abstract

Rapid thiolate exchange of dimethylarsonium, Me2As(+), is observed between two different thiolate species in solution. NMR is used to characterize the equilibrium constants for interthiol transfer as well the rapid intra molecular conformational dynamics which leads to the coalescence of diastereotopic methyl resonances. These rapid exchange kinetics have important consequences of arsenic's toxicity and pharmacology.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arsenicals / chemistry*
  • Cysteine / analogs & derivatives*
  • Glutathione / analogs & derivatives*
  • Magnetic Resonance Spectroscopy
  • Sulfhydryl Compounds / chemistry*

Substances

  • Arsenicals
  • Sulfhydryl Compounds
  • Glutathione
  • Cysteine