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.

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Metadaten
Author:Martin G. Peter, Svend Olav Andersen, Rudolf Hartmann, Merle Miessner, Peter Roepstorff
URN:urn:nbn:de:kobv:517-opus-17571
Series (Serial Number):Postprints der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe (paper 062)
Document Type:Postprint
Language:English
Date of Publication (online):2008/04/18
Year of Completion:1992
Publishing Institution:Universität Potsdam
Release Date:2008/04/18
Source:Tetrahedron. - 48 (1992), 41, p. 8927 - 8934. - ISSN 0040-4020
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Extern / Extern
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Licence (German):License LogoKeine Nutzungslizenz vergeben - es gilt das deutsche Urheberrecht
Notes extern:
first published in:
Tetrahedron. - 48 (1992), 41, p. 8927 - 8934
ISSN: 0040-4020
doi:10.1016/S0040-4020(01)81991-8