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

D'ISCHIA M.
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.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11384/84304
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