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

doi:10.1016/j.bmcl.2009.03.066

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

Applied Fine Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	2448-2452
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	19
Issue number	9
DOIs	https://doi.org/10.1016/j.bmcl.2009.03.066
Publication status	Published - 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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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.",

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AU - Furuta, Hiroyuki

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