SYNTHESIS OF ASYMMETRIC DISULFIDES AS POTENTIAL ALTERNATIVE SUBSTRATES FOR TRYPANOTHIONE REDUCTASE AND GLUTATHIONE-REDUCTASE .2.

The synthesis of asymmetrical disulfides, based on Zervas' intermediat e, monocarbobenzoxy-L-cystine, has been developed. A series of substra te analogues of trypanothione disulfide (TSST) and glutathione disulfi de (GSSG) are described, where the spermidine ring of (TSST) has been replaced by 3-dimethylaminopropylamine (DMAPA). The free amino group i n Zervas' product was condensed with phenylalanyl, tryptophanyl or glu tamyl residues, while the carbobenzoxy group was unaffected under the reaction conditions employed. The same synthetic approach was applied in the design of analogues of glutathione disulfide (GSSG).