Summary
The synthesis of asymmetrical disulfides, based on Zervas' inter-mediate, monocarbobenzoxy-L-cystine, has been developed. A series of substrate analogues of trypanothione disulfide (TSST) and glutathione disulfide (GSSG) are described, where the spermidine ring of (TSST) has been replaced by 3-dimethylaminopropylamine (DMAPA). The free amino group in Zervas' product was condensed with phenylalanyl, tryptophanyl or glutamyl 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).
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
EL-Waer A, Douglas KT, Smith K, Fairlamb AH (1991) Synthesis of N-benzyloxy-carbonyl-L-cysteinylglycine 3-dimethylaminopropylamide disulfide: a cheap and convenient new assay for trypanothione reductase. Anal Biochem 198: 212–216
Du Vigneaud V, Gish DT, Katsoyannis PG (1954) A synthetic preparation possessing biological properties associated with arginine-vasopressin. J Am Chem Soc 76: 4751–4752
Hiskey RG, Tucker WP (1962a) Chemistry of aliphatic disulfides. IV. Study on the synthesis of open-chain unsymmetrical cystine derivatives. J Am Chem Soc 84: 4789–4794
Hiskey RG, Tucker WP (1962b) Chemistry of aliphatic disulfides. V. Preparation of some open-chain unsymmetrical cystine derivatives from thioethers of cysteine. J Am Chem Soc 84: 4794–4797
Hiskey RG, Mizoguchi T, Smithwick EL Jr (1967) Chemistry of aliphatic disulfides. XII. Synthesis of open-chain unsymmetrical cystine derivatives. J Am Chem Soc 89: 97–102
Jaouhari R, Beshaya T, McKie JH, Douglas (1995) Synthesis of symmetric disulfides as potential alternative substrates for trypanothione reductase and glutathione reductase: Part 1. Amino Acids 9: 327–342
Mehta A, Jaouhari R, Benson TJ, Douglas KT (1992) Improved efficiency and selectivity in peptide synthesis: use of triethylsilane as a carbocation scavenger in deprotection of t-butyl esters and t-butoxycarbonyl-protected sites. Tetrahedron Lett 33: 5441–5444
Zervas L, Benoiton L, Weiss E, Winitz M, Greenstein JP (1959) Preparation and disulfide interchange reactions of unsymmetrical open-chain derivatives of cystine. J Am Chem Soc 81: 1729–1734
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Jaouhari, R., Besheya, T., McKie, J.H. et al. Synthesis of asymmetric disulfides as potential alternative substrates for trypanothione reductase and glutathione reductase: Part 2. Amino Acids 9, 343–351 (1995). https://doi.org/10.1007/BF00807271
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00807271