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• W2001538051 abstract "Aberrant oxidative transformations of the indolic neurotransmitter 5-hydroxytryptamine (5-HT, serotonin) might occur in serotonergic neurons in the brains of Alzheimer's disease (AD) patients. In the event that such reactions occur in serotonergic nerve terminals or axons, they would do so in the presence of glutathione (GSH). In this investigation the electrochemically driven and tyrosinase + O2-mediated oxidation of 5-HT in the presence of GSH has been studied. In the absence of GSH, 5-HT is oxidized to a C(4)-centered carbocation intermediate (9a) which reacts either with 5-HT, to give 5,5′-dihydroxy-4,4′-bitryptamine (2) as the major product along with a number of other carbon-carbon and ether-linked dimers and oligomers, or with water to give tryptamine-4,5-dione (11). In the presence of GSH this reaction is partially diverted as a consequence of nucleophilic addition of the tripeptide to 9a to give 4-S-glutathionyl-5-hydroxytryptamine (1). Other products formed include isomers of the 6-S-glutathionyl conjugates of dimer 2, 7-S-glutathionyltryptamine-4,5-dione (5) and glutathionyl conjugates of an indolic trimer and of two tetramers. Compound 1 might be a useful analytical marker molecule for unusual oxidation reactions of 5-HT in the Alzheimer brain." @default.
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• W2001538051 date "1995-02-01" @default.
• W2001538051 modified "2023-09-23" @default.
• W2001538051 title "Influence of glutathione on the electrochemical and enzymatic oxidation of serotonin" @default.
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• W2001538051 doi "https://doi.org/10.1016/0022-0728(94)03637-i" @default.
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