Facile synthesis of peptide-porphyrin conjugates: Towards artificial catalase.
A facile synthetic method for peptide-porphyrin conjugates containing four peptide units on one porphyrin was developed using chemoselective reactions. The key building blocks, 5,10,15,20-tetrakis(3-azidophenyl)porphyrin 1 and 5,10,15,20-tetrakis(5-azido-3-pyridyl)porphyrin 2, were efficiently synthesized and used as substrates for two well-known chemoselective reactions, traceless Staudinger ligation and copper-catalyzed azide alkyne cycloaddition (so-called click chemistry). Both reactions gave the desired compounds, and click chemistry was superior for our purpose. To confirm the value of the established methodology, nine peptide-porphyrin conjugates were synthesized, and their catalase- and peroxidase-like activity in water was evaluated. Our synthetic strategy is expected to be valuable for the preparation of artificial heme protein models.
Umezawa
Naoki
N
Graduate School of Pharmaceutical Sciences Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya, Aichi, Japan. umezawa@phar.nagoya-cu.ac.jp
Matsumoto
Nobuyoshi
N
Iwama
Shinsuke
S
Kato
Nobuki
N
Higuchi
Tsunehiko
T
D002374:Catalase / Q000737:chemistry*; D002384:Catalysis; D006801:Humans; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry
D010455:Peptides; D011166:Porphyrins; D002374:Catalase