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The combination of zinc dyshomoeostasis and oxidative damage has been linked to a number of human disease pathologies. A common pathway of oxidative damage centers on tyrosine with the generation of 3,4-dihydroxyphenylalanine (l-dopa). Once formed this catecholic moiety can be involved in metal binding. Herein, an l-dopa residue is incorporated into a peptide designed to adopt a β-hairpin configuration...
Posttranslational modification of tyrosine to 3,4-dihydroxyphenylalanine (dopa) yields a unique functional group in biomolecular systems. Oxidation produces a quinone, which can undergo cross linking while deprotonation is well suited to metal binding. Mussels, tunicates and bacteria chelate iron and other metals with multiple dopa subunits. Solution equilibria between catechols and iron indicate...
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