905992-17-8Relevant articles and documents
Facile synthesis of peptide-porphyrin conjugates: Towards artificial catalase
Umezawa, Naoki,Matsumoto, Nobuyoshi,Iwama, Shinsuke,Kato, Nobuki,Higuchi, Tsunehiko
experimental part, p. 6340 - 6350 (2010/10/04)
A facile synthetic method for peptide-porphyrin conjugates containing four peptide units on one porphyrin was developed using chemoselective reactions. The key building blocks, 5,10,15,20-tetrakis(3-azidophenyl)porphyrin 1 and 5,10,15,20-tetrakis(5-azido-3-pyridyl)porphyrin 2, were efficiently synthesized and used as substrates for two well-known chemoselective reactions, traceless Staudinger ligation and copper-catalyzed azide alkyne cycloaddition (so-called click chemistry). Both reactions gave the desired compounds, and click chemistry was superior for our purpose. To confirm the value of the established methodology, nine peptide-porphyrin conjugates were synthesized, and their catalase- and peroxidase-like activity in water was evaluated. Our synthetic strategy is expected to be valuable for the preparation of artificial heme protein models.
Reaction mechanism and kinetics of the traceless Staudinger ligation
Soellner, Matthew B.,Nilsson, Bradley L.,Raines, Ronald T.
, p. 8820 - 8828 (2007/10/03)
The traceless Staudinger ligation enables the formation of an amide bond between a phosphinothioester (or phosphinoester) and an azide without the incorporation of residual atoms. Here, the coupling of peptides by this reaction was characterized in detail
