STUDIES ON THIAMINE DISULFIDE : (XXI) SYNTHESIS OF THIAMINE-GLUTATHIONE MIXED DISULFIDE AND ITS BIOLOGICAL PROPERTIES

Abstract

Although TGD has long been assumed as the intermediate product in the reaction of TDS and GSH, its isolation has not been achieved. In this study, TGD and its O-benzyl derivative, BTGD, were successfully synthesized and isolated as the colorless crystals, mp. 179-181℃ (decomp.) and 172-174℃ (decomp.), by the reaction between TDSO (BTDSO) and GSH. The newly synthesized compounds were confirmed by IR-, UV-spectrum, PPC, PEP and elementary analysis. TGD was tested for prevention of thiamine deficiency in Uroloncha domestica and was confirmed to possess the same efficacy as that of thiamine. The significance of the compound as the intermediary metabolite of TDS derivatives, was also discussed on the basis of the equilibrium constant estimated in the exchange reaction between the compound and GSH.