Elsevier

Bioorganic Chemistry

Volume 24, Issue 2, June 1996, Pages 127-149
Bioorganic Chemistry

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

https://doi.org/10.1006/bioo.1996.0012Get rights and content

Abstract

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-glutathionyl-tryptophan-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 of5in a reaction where the glutathionyl residue migrates from the C(4)- to the C(7)-position. In the presence of free GSH7reacts to give the 3,7- and 6,7-bi-S-glutathionyl conjugates of4and, 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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