Cyclic Structural Motifs in 5,6-Dihydroxyindole Polymerization Uncovered: Biomimetic Modular Buildup of a Unique Five-Membered Macrocycle
2010; American Chemical Society; Volume: 12; Issue: 14 Linguagem: Inglês
10.1021/ol101188c
ISSN1523-7060
AutoresMarianna Arzillo, Alessandro Pezzella, Orlando Crescenzi, Alessandra Napolitano, Edward J. Land, Vincenzo Barone, Marco d’Ischia,
Tópico(s)Porphyrin and Phthalocyanine Chemistry
ResumoAn unprecedented 5,6-dihydroxyindole macrocycle (4) featuring a rigid twisted backbone was obtained by biomimetic oxidative cross-coupling of the 2,2′-biindole 2 and triindole 3. A putative reaction intermediate, 2-quinone, was detected and characterized by pulse radiolysis and DFT calculations. Discovery of 4 indirectly supports for the first time theoretically predicted cyclic structural motifs as potential eumelanin building blocks.
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