Facile synthesis of peptide-porphyrin conjugates: Towards artificial catalase

Naoki Umezawa, Nobuyoshi Matsumoto, Shinsuke Iwama, Nobuki Kato, Tsunehiko Higuchi

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)6340-6350
Number of pages11
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number17
DOIs
Publication statusPublished - 2010 Sep 1
Externally publishedYes

Keywords

  • Catalase
  • Click chemistry
  • Peptide
  • Porphyrin
  • Staudinger ligation

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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