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

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

Fingerprint

All Science Journal Classification (ASJC) codes

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

Cite this

Ikawa, Y., Harada, H., Toganoh, M., & Furuta, H. (2009). Synthesis and protonation behavior of a water-soluble N-fused porphyrin: Conjugation with an oligoarginine by click chemistry. Bioorganic and Medicinal Chemistry Letters, 19(9), 2448-2452. https://doi.org/10.1016/j.bmcl.2009.03.066

@article{447fd2b6b38f4d2e9d09222d6dc732d2,

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

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.",

author = "Yoshiya Ikawa and Hiroyuki Harada and Motoki Toganoh and Hiroyuki Furuta",

year = "2009",

month = "5",

day = "1",

doi = "10.1016/j.bmcl.2009.03.066",

language = "English",

volume = "19",

pages = "2448--2452",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

number = "9",

}

TY - JOUR

T1 - Synthesis and protonation behavior of a water-soluble N-fused porphyrin

T2 - Conjugation with an oligoarginine by click chemistry

AU - Ikawa, Yoshiya

AU - Harada, Hiroyuki

AU - Toganoh, Motoki

AU - Furuta, Hiroyuki

PY - 2009/5/1

Y1 - 2009/5/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=64249084533&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=64249084533&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2009.03.066

DO - 10.1016/j.bmcl.2009.03.066

M3 - Article

C2 - 19349180

AN - SCOPUS:64249084533

VL - 19

SP - 2448

EP - 2452

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 9

ER -

Access to Document

10.1016/j.bmcl.2009.03.066