Synthesis and protonation behavior of a water-soluble N-fused porphyrin: conjugation with an oligoarginine by click chemistry.
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.
Ikawa
Yoshiya
Y
Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, 744 Moto-oka, Nishi-Ku Fukuoka 819-0395, Japan.
Harada
Hiroyuki
H
Toganoh
Motoki
M
Furuta
Hiroyuki
H
D000480:Alkynes / Q000737:chemistry; D001120:Arginine / Q000737:chemistry*; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D003300:Copper / Q000737:chemistry; D015195:Drug Design; D006863:Hydrogen-Ion Concentration; D057927:Hydrophobic and Hydrophilic Interactions; D008956:Models, Chemical; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry; D011166:Porphyrins / Q000737:chemistry*; D011522:Protons; D012995:Solubility; D013055:Spectrophotometry, Infrared / Q000379:methods; D014867:Water / Q000737:chemistry*
D000480:Alkynes; D010455:Peptides; D011166:Porphyrins; D011522:Protons; D014867:Water; D003300:Copper; D001120:Arginine