Proton, carbon-13, and phosphorus-31 nuclear magnetic resonance studies of (2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosato-S)(triethylphosphine)gold (auranofin), a novel antiarthritic agent

Abstract

The ¹H and ¹³C high-field n.m.r. spectra of auranofin in a variety of aqueous and non-aqueous solvents have been analysed and all peaks unambiguously assigned except those for the acetyl groups. Specific solvation and co-ordination shifts are discussed. The conformation in solution appears to resemble that in the crystal, with the glucopyranose ring in a chair form. Phosphorus-31 n.m.r. studies suggest that auranofin is relatively stable at pH 7 and 4, but not at pH 1.