title: Role of linkers in tertiary amines that mediate or catalyze 1,3,5-triazine-based amide-forming reactions.
abstract: We studied 1,3,5-triazine-based amide-forming reactions that are mediated or catalyzed by various tert-amines. The representative tert-amine was trimethylamine, which has amido, 1,2,3-triazolyl, aryl, and alkyl linkers. It was found that electron-deficient aryl and heteroaryl linkers, particularly 1,2,3-triazolyl linkers, are superior. On the basis of our findings, we synthesized ligand catalysts, including a 1,2,3-triazolyl linker that connects a protein ligand to a trimethylamine moiety, and found that fluorescent-labeling of a targeting protein using the ligand catalysts proceeded in good yields.
authors.affiliation: Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University , Kakuma-machi, Kanazawa 920-1192, Japan.
authors.forename: Masanori
authors.initials: M
authors.lastname: Kitamura
authors.forename: Fumitaka
authors.initials: F
authors.lastname: Kawasaki
authors.forename: Kouichi
authors.initials: K
authors.lastname: Ogawa
authors.forename: Shuichi
authors.initials: S
authors.lastname: Nakanishi
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Tanaka
authors.forename: Kohei
authors.initials: K
authors.lastname: Yamada
authors.forename: Munetaka
authors.initials: M
authors.lastname: Kunishima
mesh_terms: D000577:Amides / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D008024:Ligands; D008744:Methylamines / Q000737:chemistry*; D015394:Molecular Structure; D014227:Triazines / Q000737:chemistry*
chemical_list: D000577:Amides; D000588:Amines; D008024:Ligands; D008744:Methylamines; D014227:Triazines; C023336:trimethylamine