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The first expedient entry to the human melanogen 2-S-cysteinyldopa exploiting the anomalous regioselectivity of 3,4-dihydroxycinnamic acid-thiol conjugation
Authors:Lucia Panzella,Marco d&rsquo  Ischia
Affiliation:Department of Organic Chemistry and Biochemistry, University of Naples Federico II, Complesso Universitario Monte S. Angelo, I-80126 Naples, Italy
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.
Keywords:Cysteinyldopas   Thiol conjugation   Pheomelanin   3,4-Dihydroxycinnamic acid derivatives
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