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7-S-Glutathionyltryptophan-4,5-dione: Formation from 5-Hydroxytryptophan and Reactions with Glutathione

✍ Scribed by Zheng Wu; Glenn Dryhurst

Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
344 KB
Volume
24
Category
Article
ISSN
0045-2068

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✦ Synopsis

The electrochemically driven oxidation of 5-hydroxytryptophan (5-HTPP) in the presence of free glutathione (GSH) yields 4-S-glutathionyl-5-hydroxytryptophan (5) and 7-S-glutathionyltryptophan-4,5-dione (7). The latter glutathionyl conjugate is formed both by nucleophilic addition of GSH to tryptophan-4,5-dione (4), a normal product of the oxidation of 5-HTPP, and by oxidation of 5 in a reaction where the glutathionyl residue migrates from the C(4)to the C(7)-position. In the presence of free GSH 7 reacts to give the 3,7-and 6,7-bi-Sglutathionyl conjugates of 4 and, as a result of intramolecular cyclization reactions, a number of glutathionyl conjugates of an unusual tricyclic pyrroloquinoline. It is speculated that one or more of these products might represent aberrant oxidative metabolites that have been detected in the cerebrospinal fluid of patients with Alzheimer's Disease.

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