INFLUENCE OF L-CYSTEINE AND N-ACETYL-L-CYSTEINE ON REDUCING ACTIVITY OF THIOUREA DIOXIDE IN AQUEOUS SOLUTIONS

Abstract

The influence of L-cysteine and N-acetyl-L-cysteine on the stability and reducing activity of thiourea dioxide (NH2)2CSO2 (TDO) in the reaction with azo dye Orange II has been studied. The addition of L-cysteine and N-acetyl-L-cysteine leads to the increase in reducing activity of TDO in weakly acidic, neutral and weakly alkaline solutions, but does not influence its reducing activity in strongly alkaline solutions. In alkaline solutions, the rate of reduction of Orange II is increasing, but the influence of additives of thiol acids is decreasing. The activating effect of N-ace-tyl-L-cysteine is weaker than the effect of L-cysteine, that can be explained by the differences of pKa of these acids. Indeed, the reducing activity of thiols depends on the concentration of thiolate-ions in solutions. Since pKa of cysteine (8.30) is significantly less than pKa of  N-acetyl-L-cysteine (9.52), concentration of thiolate-ions in cysteine solutions is higher. Therefore, reducing activity of L-cysteine is higher.  The influence of L-cysteine and N-acetyl-L-cysteine on the reaction of TDO with Orange II is different from the influence of aminoacid glycine: in neutral solutions glycine decreases the rate of reaction. The interaction of TDO with L-cysteine in weakly acidic, neutral and weakly alkaline solutions is accompanied by the oxidation of L-cysteine to cysteinesulfenic acid and reduction of TDO to thiourea monoxide (NH2)2CSO. Then cysteinesulfenic acid reacts with L-cysteine with formation of cystine. The reaction studied here is the first example of reduction of TDO by sulfur-containing compounds.