Oxidation of the neurotoxin 6-nitrodopamine and related 4-nitrocatechols under biomimetic conditions

Authors
Napolitano, A Palumbo, A d'Ischia, M
Citation
A. Napolitano et al., Oxidation of the neurotoxin 6-nitrodopamine and related 4-nitrocatechols under biomimetic conditions, TETRAHEDRON, 56(32), 2000, pp. 5941-5945
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
32
Year of publication
2000
Pages
5941 - 5945
Database
ISI
SICI code
0040-4020(20000804)56:32<5941:OOTN6A>2.0.ZU;2-2
Abstract
Oxidation of 6-nitrodopamine (1) with horseradish peroxidase (HRP)/H2O2 in 0.05 M phosphate buffer, pH 7.4 afforded as main product the novel 5-[4-(2- aminoethyl)-2-hydroxy-5-nitrophenoxy]-6,7-dihydroxy-4-nitro-2,3-dihydroindo le (4). Similar oxidation of the 4-nitrocatechols 2 and 3 with HRP/H2O2 or K3Fe(CN)(6) gave chiefly the dimers 5/6 and 7/8. These products arise proba bly via 4-nitro-o-quinone or 4-nitro-2,3-dihydroindole-6,7-dione intermedia tes which are trapped by the starting nitrocatechols. (C) 2000 Elsevier Sci ence Ltd. All rights reserved.