title: Horseradish-Peroxidase-Catalyzed Tyrosine Click Reaction.
abstract: The efficiency of protein chemical modification on tyrosine residues with N-methylluminol derivatives was drastically improved by using horseradish peroxidase (HRP). In the previous method, based on the use of hemin and H2O2, oxidative side reactions such as cysteine oxidation were problematic for functionalization of proteins selectively on tyrosine residues. Oxidative activation of N-methylluminol derivatives with a minimum amount of H2O2prevented the occurrence of oxidative side reactions under HRP-catalyzed conditions. As probes for HRP-catalyzed protein modification, N-methylluminol derivatives showed much higher efficiency than tyramide without inducing oligomerization of probe molecules. Tyrosine modification also proceeded in the presence of β-nicotinamide adenine dinucleotide (NADH, H2O2-free conditions).
authors.affiliation: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, Yokohama, 226-8503, Japan.
authors.forename: Shinichi
authors.identifier: 0000-0002-8563-1658
authors.initials: S
authors.lastname: Sato
authors.affiliation: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, Yokohama, 226-8503, Japan.
authors.forename: Kosuke
authors.initials: K
authors.lastname: Nakamura
authors.affiliation: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, Yokohama, 226-8503, Japan.
authors.forename: Hiroyuki
authors.identifier: 0000-0002-4511-2984
authors.initials: H
authors.lastname: Nakamura
mesh_terms: D001665:Binding Sites; D002384:Catalysis; D057930:Click Chemistry; D006418:Heme / Q000737:chemistry; D006735:Horseradish Peroxidase / Q000737:chemistry / Q000378:metabolism*; D006861:Hydrogen Peroxide / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D014443:Tyrosine / Q000737:chemistry*
chemical_list: D014443:Tyrosine; D006418:Heme; D006861:Hydrogen Peroxide; D006735:Horseradish Peroxidase
keywords: heme proteins; horseradish peroxidase; protein labeling; protein modifications; tyrosine modification