Ligand-Directed Selective Protein Modification Based on Local Single-Electron-Transfer Catalysis

• Published in: Angewandte Chemie (International ed.) Vol. 52; no. 33; pp. 8681 - 8684
• Main Authors: Sato, Shinichi, Nakamura, Hiroyuki
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 12.08.2013; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Angiotensin II - chemistry; Animals; Carbonic Anhydrases - chemistry; Catalysis; Catalysts; Cattle; Cells, Cultured; Chemistry; Chemistry, Multidisciplinary; Electron Transport; Electrons; Erythrocytes - enzymology; Female; Fluorescent Dyes; Formations; Free Radical Scavengers - chemistry; Ligands; Mice; Molecular Structure; photocatalysts; Physical Sciences; protein modifications; Proteins; Pyridines - chemistry; radical reactions; Radicals; Reagents; Ruthenium - chemistry; Science & Technology; Serum Albumin, Bovine - chemistry; single-electron transfer; Trapping; tyrosine; Tyrosine - analogs & derivatives; Tyrosine - chemistry; CELLS; protein modifications; BIOCONJUGATION; ALKYLATION; photocatalysts; LIGHT; radical reactions; CHEMISTRY; single-electron transfer; tyrosine; RHODIUM CARBENOIDS; DAMAGE
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201303831

A photocatalyst ([Ru(bpy)3]2+) bound to a protein ligand was essential for the title method. Local single‐electron transfer from the catalyst resulted in the formation of tyrosyl radicals. N′‐Acetyl‐N,N‐dimethyl‐1,4‐phenylenediamine was used as the tyrosyl radical trapping agent and used in a radical addition to afford selective modification of the target protein.