Biomimetic oxidn. of the pheomelanin precursor 5-S-cysteinyldopa in the presence of Zn2+ ions led to the isolation of two isomeric products, one of which could be identified as the benzothiazolylthiazinodihydroisoquinoline 5, while the other proved too unstable for a complete characterization. Both these products were converted into more stable oxidized forms, which after ethylchloroformate derivatization were characterized as the Et ester/ethoxycarbonyl isoquinolines 8 and 9. Compd. 5 exhibited absorption characteristics similar to those of red hair pheomelanin, including a main band around 400 nm in acids. Similarly to red hair pheomelanin and synthetic pigments, 5 afforded on chem. degrdn. a thiazolylpyridinecarboxylic acid fragment. Model chem. studies allowed the proposal of a formation mechanism for the benzothiazole and dihydroisoquinoline systems in compd. 5.

Uncovering the structure of human red hair pheomelanin: benzothiazolylthiazinodihydroisoquinolines as key building blocks / Greco, Giorgia; Panzella, Lucia; Verotta, L.; D'Ischia, Marco; Napolitano, Alessandra. - In: JOURNAL OF NATURAL PRODUCTS. - ISSN 0163-3864. - 74:4(2011), pp. 675-682. [10.1021/np100740n]

Uncovering the structure of human red hair pheomelanin: benzothiazolylthiazinodihydroisoquinolines as key building blocks.

GRECO, GIORGIA;PANZELLA, LUCIA;D'ISCHIA, MARCO;NAPOLITANO, ALESSANDRA
2011

Abstract

Biomimetic oxidn. of the pheomelanin precursor 5-S-cysteinyldopa in the presence of Zn2+ ions led to the isolation of two isomeric products, one of which could be identified as the benzothiazolylthiazinodihydroisoquinoline 5, while the other proved too unstable for a complete characterization. Both these products were converted into more stable oxidized forms, which after ethylchloroformate derivatization were characterized as the Et ester/ethoxycarbonyl isoquinolines 8 and 9. Compd. 5 exhibited absorption characteristics similar to those of red hair pheomelanin, including a main band around 400 nm in acids. Similarly to red hair pheomelanin and synthetic pigments, 5 afforded on chem. degrdn. a thiazolylpyridinecarboxylic acid fragment. Model chem. studies allowed the proposal of a formation mechanism for the benzothiazole and dihydroisoquinoline systems in compd. 5.
2011
Uncovering the structure of human red hair pheomelanin: benzothiazolylthiazinodihydroisoquinolines as key building blocks / Greco, Giorgia; Panzella, Lucia; Verotta, L.; D'Ischia, Marco; Napolitano, Alessandra. - In: JOURNAL OF NATURAL PRODUCTS. - ISSN 0163-3864. - 74:4(2011), pp. 675-682. [10.1021/np100740n]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/382342
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