R. Jaouhari et al., SYNTHESIS OF ASYMMETRIC DISULFIDES AS POTENTIAL ALTERNATIVE SUBSTRATES FOR TRYPANOTHIONE REDUCTASE AND GLUTATHIONE-REDUCTASE .2., Amino acids, 9(4), 1995, pp. 343-351
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de (GSSG) are described, where the spermidine ring of (TSST) has been
replaced by 3-dimethylaminopropylamine (DMAPA).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).