Synthesis, Characterisation and Reactivity of 3-Mercaptopyruvic Acid.

The synthesis, isolation and spectroscopic characterisation of the sulfur metabolic compound 3-mercaptopyruvic acid (3-MPH) is reported, for the first time. The compound is isolated without tedious workup, with a purity of 97 %, as indicated by chemical and biochemical analyses. Detailed kinetic and thermodynamic studies of its complex behaviour in solution are discussed. 3-MPH is stable in the enol form in non-polar solvent. In polar solvent, a fast equilibrium between the α-ketoacid and a cyclic dimer dithiane is observed. The formation of the dimer confers increased stability to 3-MPH towards hydrogen peroxide, in comparison with cysteine.