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Title: | Synthesis and antioxidant activity of DOPA peptidomimetics by a novel IBX mediated aromatic oxidative functionalization | Authors: | Bizzarri, Bruno Mattia Pieri, Cristina Botta, Giorgia Arabuli, Lili Mosesso, Pasquale Cinelli, Serena Schinoppi, Angelo Saladino, Raffele |
Journal: | RSC ADVANCES | Issue Date: | 2015 | Abstract: | 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 H |
URI: | http://hdl.handle.net/2067/42754 | ISSN: | 2046-2069 | DOI: | 10.1039/c5ra09464j | Rights: | CC0 1.0 Universal |
Appears in Collections: | A1. Articolo in rivista |
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Synthesis and antioxidant activity of DOPA RSC Adv., 2015, 5, 60354.pdf | 716.82 kB | Adobe PDF | Request a copy |
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