title: New molecular motif for recognizing sialic acid using emissive lanthanide-macrocyclic polyazacarboxylate complexes: deprotonation of a coordinated water molecule controls specific binding.
abstract: A new molecular motif--lanthanide-macrocyclic polyazacarboxylate hexadentate complexes, Ln(3+)-ABNOTA--was found to specifically bind to sialic acid with strong emission enhancement and high affinity. The selectivity toward sialic acid over other monosaccharides was one of the highest among artificial receptors. Also, the novel binding mechanism was investigated in detail; binding selectivity is controlled by interactions between sialic acid and both the central metal and a hydroxyl group produced by deprotonation of a coordinated water molecule in the Ln(3+) complex.
authors.affiliation: Graduate School of Science and Engineering, Saitama University, 255 Shimo-Okubo, Sakura-ku, Saitama, Japan.
authors.forename: Kazuki
authors.initials: K
authors.lastname: Ouchi
authors.forename: Shingo
authors.initials: S
authors.lastname: Saito
authors.forename: Masami
authors.initials: M
authors.lastname: Shibukawa
mesh_terms: D001372:Aza Compounds / Q000737:chemistry; D001665:Binding Sites; D002264:Carboxylic Acids / Q000737:chemistry; D028581:Lanthanoid Series Elements / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry*; D011522:Protons; D014867:Water / Q000737:chemistry*
chemical_list: D001372:Aza Compounds; D002264:Carboxylic Acids; D028581:Lanthanoid Series Elements; D047028:Macrocyclic Compounds; D009942:Organometallic Compounds; D011108:Polymers; D011522:Protons; D014867:Water; D019158:N-Acetylneuraminic Acid