Synthesis and protonation behavior of a water-soluble N-fused porphyrin: Conjugation with an oligoarginine by click chemistry

Yoshiya Ikawa, Hiroyuki Harada, Motoki Toganoh, Hiroyuki Furuta

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24 Citations (Scopus)

Abstract

A water-soluble derivative of N-fused porphyrin (NFP) possessing a nona-arginine (R9) peptide tail was synthesized for the first time by a Cu(I)-catalyzed azide-alkyne 'click' reaction. In aqueous solution, at pH 8, the conjugated molecule (NFP-R9) exists as free base and protonated below pH < 6.5 to form monoprotonated species dominantly, and diprotonated one below pH < 2.3, while such clear two-step protonation behavior was not observed in the DMF solution.

Original languageEnglish
Pages (from-to)2448-2452
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number9
DOIs
Publication statusPublished - May 1 2009

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All Science Journal Classification (ASJC) codes

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

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