Tetrahedron p. 2083 - 2088 (1986)
Update date:2022-08-11
Topics:
Corradini, Maria Grazia
Napolitano, Alessandra
Prota, Giuseppe
Enzymic oxidation, or autooxidation at pH 9, of 1 led to a mixture of fluorescent products the major of which could be isolated, as the acetyl derivative, and identified as 5,6,5',6'-tetraacetoxy-1,1'-dimethyl-2,4'-biindolyl (6).In the presence of metal cations, e.g.Ni(2+), autooxidation of 1, at pH 7.5, led to the isolation, besides the dimer 6 in lower amounts, of two more oligomers which were formulated as 5,6,5',6'-tetracetoxy-1,1'-dimethyl-2,2'-biindolyl (7) and 5,6-diacetoxy-1-methyl-2,4-di-<5',6'-diacetoxy-1'-methyl-2'-indolyl>-indole (8).The unexpected reactivity of 1 to undergo oxidative coupling at 2- and 4- position rather than at 3- and 7- position, as previously believed, is discussed in relation to the current views on the structure and biosynthesis of eumelanins.
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