Facile synthesis of peptide-porphyrin conjugates: Towards artificial catalase

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

研究成果: Article査読

34 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)6340-6350
ページ数11
ジャーナルBioorganic and Medicinal Chemistry
18
17
DOI
出版ステータスPublished - 2010 9 1
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 分子医療
  • 分子生物学
  • 薬科学
  • 創薬
  • 臨床生化学
  • 有機化学

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