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

被引：15

作者：

Bizzarri, Bruno Mattia ^{[1
]}

Pieri, Cristina ^{[1
]}

Botta, Giorgia ^{[1
]}

Arabuli, Lili ^{[3
]}

Mosesso, Pasquale ^{[1
]}

Cinelli, Serena ^{[2
]}

Schinoppi, Angelo ^{[1
]}

Saladino, Raffele ^{[1
]}

机构：

[1] Univ Tuscia, Dept Ecol & Biol, Via S Camillo Lellis, I-01100 Viterbo, Italy

[2] Res Toxicol Ctr Menarini, I-00040 Pomezia, Roma, Italy

[3] Javakhishvili Tbilisi State Univ, Dept Chem, Tbilisi, Georgia

来源：

RSC ADVANCES | 2015年 / 5卷 / 74期

关键词：

CROSS-LINKING; REGIOSELECTIVE OXIDATION; POTENTIAL IMPLICATIONS; CONTAINING PEPTIDES; AMINO-ACIDS; TYROSINASE; PROTEINS; IDENTIFICATION; DERIVATIVES; ACTIVATION;

D O I：

10.1039/c5ra09464j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：60354 / 60364

页数：11

共 54 条

[21] pH-dependent cross-linking of catechols through oxidation via Fe3+ and potential implications for mussel adhesion [J].