Synthesis of asymmetric disulfides as potential alternative substrates for trypanothione reductase and glutathione reductase: Part 2 |
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Authors: | R. Jaouhari T. Besheya J. H. McKie K. T. Douglas |
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Affiliation: | (1) Pharmacy Department, University of Manchester, Manchester, United Kingdom;(2) QUCHEM, School of Chemistry, The Queen's University of Belfast, David Keir Building, Belfast, BT9 5AG Northern Ireland, UK |
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Abstract: | 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trypanothione disulfide (TSST) and glutathione disulfide (GSSG) are described, where the spermidine ring of (TSST) has been replaced by 3-dimethylaminopropylamine (DMAPA).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). |
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Keywords: | Amino acids Synthesis Symmetrical disulfide Trypanothione reductase Glutathione reductase |
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