The first tetramer of the eumelanin precursor 5,6-dihydroxyindole has been obtained, as the acetyl derivative, by peroxidase/H2O2-induced oxidative coupling of 5,5',6,6'-tetrahydroxy-2,4'-biindolyl (2) in the presence of Zn2+ ions. The tetramer, 5,5',5' ',5' '',6,6',6' ',6' ''-octaacetoxy-2,4':2',3' ':2' ',4' ''-tetraindolyl (acetylated 7), incorporates an unprecedented 2,3'-biindolyl substructure suggestive of a different positional reactivity of the 5,6-dihydroxyindole system when framed into a dimeric scaffold
The First 5,6-Dihydroxyindole Tetramer by Oxidation of 5,5',6,6'-Tetrahydroxy- 2,4'-biindolyl and an Unexpected Issue of Positional Reactivity en Route to Eumelanin-Related Polymers / Panzella, Lucia; Pezzella, Alessandro; Napolitano, Alessandra; D'Ischia, Marco. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - 9:7(2007), pp. 1411-1414. [10.1021/ol070268w]
The First 5,6-Dihydroxyindole Tetramer by Oxidation of 5,5',6,6'-Tetrahydroxy- 2,4'-biindolyl and an Unexpected Issue of Positional Reactivity en Route to Eumelanin-Related Polymers.
PANZELLA, LUCIA;PEZZELLA, ALESSANDRO;NAPOLITANO, ALESSANDRA;D'ISCHIA, MARCO
2007
Abstract
The first tetramer of the eumelanin precursor 5,6-dihydroxyindole has been obtained, as the acetyl derivative, by peroxidase/H2O2-induced oxidative coupling of 5,5',6,6'-tetrahydroxy-2,4'-biindolyl (2) in the presence of Zn2+ ions. The tetramer, 5,5',5' ',5' '',6,6',6' ',6' ''-octaacetoxy-2,4':2',3' ':2' ',4' ''-tetraindolyl (acetylated 7), incorporates an unprecedented 2,3'-biindolyl substructure suggestive of a different positional reactivity of the 5,6-dihydroxyindole system when framed into a dimeric scaffold| File | Dimensione | Formato | |
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