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Bizzarri B.M.,University of Tuscia | Pieri C.,University of Tuscia | Botta G.,University of Tuscia | Arabuli L.,Tbilisi State University | And 4 more authors.
RSC Advances | Year: 2015

DOPA peptidomimetics with stable O-C and N-C covalent bonds between amino acid residues have been prepared by aromatic oxidative functionalization of tyrosine with 2-iodoxybenzoic acid (IBX). The reaction involves the Michael-like nucleophilic addition of different oxygen and nitrogen protected amino acids on a reactive DOPA quinone intermediate. Similar results were obtained in heterogeneous conditions using supported IBX-amide for more runs. Among the novel derivatives, compounds containing glycine residues showed a more pronounced antioxidant activity in the 2,2-diphenyl picrylhydrazyl (DPPH) radical scavenging cell free assay. Instead, valine derivatives showed the highest biological effect in L5178Y mouse lymphoma cells, by assessing the ability to reduce H2O2 induced DNA breakage in the alkaline comet assay. © The Royal Society of Chemistry 2015.

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