Synthesis of Dithiols as Reducing Agents for Disulfides in Neutral Aqueous Solution and Comparison of Reduction Potentials

Article abstract of DOI:10.1021/jo00055a015

Several dithiols have been prepared that are useful for the reduction of disulfides in aqueous solution.The reduction potential of these thiols have been determined from the measurement of the equilibrium constant of thiol/disulfide interchange with oxidized dithiothreitol using a 1H NMR assay.The values of pK_a of some of the dithiols were measured to estimate their rate of reduction of disulfides.Bis(2-mercaptoethyl) sulfone (2), N,N'-dimethyl-N,N'-bis(mercaptoacetyl)hydrazine (5), and meso-2,5-dimercapto-N,N,N',N'-tetramethyladipamide (6) are especially interesting as alternatives to dithiothreitol for the reduction of disulfides.