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Catecholamine-protein conjugates : isolation of 4-phenylphenoxazin-2-ones from oxidative coupling of N-acetyldopamine with alipathic amino acids

4-Phenylphenoxazinones were isolated after biomimetic oxidation, using diphenoloxidases of insect cuticle, mushroom tyrosinase, or after autoxidation of N-acetyldopamine (Image ) in the presence of β-alanine, β-alanine methyl ester or N-acetyl-L-lysine. They are formed presumably by addition of 2-aminoalkyl-5-alkylphenols to the o-quinone of biphenyltetrol which, in turn, arises from oxidative coupling of. The structures of present the first examples for the assembly of reasonably stable intermediates in the rather complex process of chemical modifications of aliphatic amino acid residues by o-quinones.

Identiferoai:union.ndltd.org:Potsdam/oai:kobv.de-opus-ubp:1757
Date January 1992
CreatorsPeter, Martin G., Andersen, Svend Olav, Hartmann, Rudolf, Miessner, Merle, Roepstorff, Peter
PublisherUniversität Potsdam, Mathematisch-Naturwissenschaftliche Fakultät. Institut für Chemie, Extern. Extern
Source SetsPotsdam University
LanguageEnglish
Detected LanguageEnglish
TypePostprint
Formatapplication/pdf
SourceTetrahedron. - 48 (1992), 41, p. 8927 - 8934. - ISSN 0040-4020
Rightshttp://opus.kobv.de/ubp/doku/urheberrecht.php

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