title: Facile synthesis of peptide-porphyrin conjugates: Towards artificial catalase.
abstract: 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.
authors.affiliation: Graduate School of Pharmaceutical Sciences Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya, Aichi, Japan. umezawa@phar.nagoya-cu.ac.jp
authors.forename: Naoki
authors.initials: N
authors.lastname: Umezawa
authors.forename: Nobuyoshi
authors.initials: N
authors.lastname: Matsumoto
authors.forename: Shinsuke
authors.initials: S
authors.lastname: Iwama
authors.forename: Nobuki
authors.initials: N
authors.lastname: Kato
authors.forename: Tsunehiko
authors.initials: T
authors.lastname: Higuchi
mesh_terms: D002374:Catalase / Q000737:chemistry*; D002384:Catalysis; D006801:Humans; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D010455:Peptides; D011166:Porphyrins; D002374:Catalase