Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 19, Issue 9, Pages 2448-2452Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2009.03.066
Keywords
N-Fused porphyrin; Water-soluble porphyrin; Oligoarginine; Click chemistry; Protonation
Categories
Funding
- Young Scientists (A) [18685020]
- Exploratory Research [19657071]
- [19750036]
- Grants-in-Aid for Scientific Research [19657071, 18685020] Funding Source: KAKEN
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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. (c) 2009 Elsevier Ltd. All rights reserved.
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