Details

Autor(en) / Beteiligte

• Bizzarri, Bruno Mattia
• Pieri, Cristina
• Botta, Giorgia
• Arabuli, Lili
• Mosesso, Pasquale
• Cinelli, Serena
• Schinoppi, Angelo
• Saladino, Raffele

Titel

Synthesis and antioxidant activity of DOPA peptidomimetics by a novel IBX mediated aromatic oxidative functionalization

Ist Teil von

• RSC advances, 2015-01, Vol.5 (74), p.60354-60364

Erscheinungsjahr

2015

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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 sub(2)O sub(2) induced DNA breakage in the alkaline comet assay.