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