Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2067/42754
Titolo: Synthesis and antioxidant activity of DOPA peptidomimetics by a novel IBX mediated aromatic oxidative functionalization
Autori: Bizzarri, Bruno Mattia 
Pieri, Cristina
Botta, Giorgia
Arabuli, Lili
Mosesso, Pasquale 
Cinelli, Serena
Schinoppi, Angelo
Saladino, Raffele
Rivista: RSC ADVANCES 
Data pubblicazione: 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 H2O2 induced DNA breakage in the alkaline comet assay.
URI: http://hdl.handle.net/2067/42754
ISSN: 2046-2069
DOI: 10.1039/c5ra09464j
Diritti: CC0 1.0 Universal
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