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Titolo:
7-S-GLUTATHIONYLTRYPTOPHAN-4,5-DIONE - FORMATION FROM 5-HYDROXYTRYPTOPHAN AND REACTIONS WITH GLUTATHIONE
Autore:
WU Z; DRYHURST G;
Indirizzi:
UNIV OKLAHOMA,DEPT CHEM & BIOCHEM NORMAN OK 73019 UNIV OKLAHOMA,DEPT CHEM & BIOCHEM NORMAN OK 73019
Titolo Testata:
Bioorganic chemistry
fascicolo: 2, volume: 24, anno: 1996,
pagine: 127 - 149
SICI:
0045-2068(1996)24:2<127:7-FF5>2.0.ZU;2-B
Fonte:
ISI
Lingua:
ENG
Soggetto:
ALZHEIMERS-DISEASE; ENZYMATIC OXIDATION; ABERRANT METABOLITE; SEROTONIN; CHEMISTRY; SYSTEM; STRESS; BRAIN;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Science Citation Index Expanded
Citazioni:
20
Recensione:
Indirizzi per estratti:
Citazione:
Z. Wu e G. Dryhurst, "7-S-GLUTATHIONYLTRYPTOPHAN-4,5-DIONE - FORMATION FROM 5-HYDROXYTRYPTOPHAN AND REACTIONS WITH GLUTATHIONE", Bioorganic chemistry, 24(2), 1996, pp. 127-149

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 7S-glutathionyltryptophan-4,5-dione (7). Thelatter glutathionyl conjugate is formed both by nucleophilic additionof GSH to tryptophan-4,5-dione (4), a normal product of the oxidationof 5-HTPP, and by oxidation of 5 in a reaction where the glutathionylresidue migrates from the C(4)- to the C(7)-position. In the presenceof free GSH 7 reacts to give the 3,7- and 6,7-bi-S-glutathionyl conjugates of 4 and, as a result of intramolecular cyclization reactions, anumber 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. (C) 1996 Academic Press, Inc.

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Documento generato il 29/11/20 alle ore 00:42:35