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

    Research output: Contribution to journalArticlepeer-review

    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

    All Science Journal Classification (ASJC) codes

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

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