The first convenient synthesis of 2-S-cysteinyl-3,4-dihydroxyphenylalanine (2-S-cysteinyldopa) in 30% overall yield is reported, which capitalizes on the anomalous regiochemistry of the oxidative coupling of 3,4-dihydroxycinnamic acid derivatives with thiol compounds, leading to 2-S rather than the usual 5-S conjugates. (C) 2007 Elsevier Ltd. All rights reserved.
The first expedient entry to the human melanogen 2-S-cysteinyldopa exploiting the anomalous regioselectivity of 3,4-dihydroxycinnamic acid-thiol conjugation / Panzella, Lucia; DE LUCIA, M.; Napolitano, Alessandra; D'Ischia, Marco. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 48:43(2007), pp. 7650-7652. [10.1016/j.tetlet.2007.08.098]
The first expedient entry to the human melanogen 2-S-cysteinyldopa exploiting the anomalous regioselectivity of 3,4-dihydroxycinnamic acid-thiol conjugation.
PANZELLA, LUCIA;NAPOLITANO, ALESSANDRA;D'ISCHIA, MARCO
2007
Abstract
The first convenient synthesis of 2-S-cysteinyl-3,4-dihydroxyphenylalanine (2-S-cysteinyldopa) in 30% overall yield is reported, which capitalizes on the anomalous regiochemistry of the oxidative coupling of 3,4-dihydroxycinnamic acid derivatives with thiol compounds, leading to 2-S rather than the usual 5-S conjugates. (C) 2007 Elsevier Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
