title: Discovery of a sensitive Cu(II)-cyanide "off-on" sensor based on new C-glycosyl triazolyl bis-amino acid scaffold.
abstract: A new functional glycosyl peptidomimetic, featuring a C-glucosyl 1,4-dimethoxynaphthalene backbone in conjugation with two triazolyl phenylalanine moieties on its adjacent C3,4-positions, was readily synthesized via click chemistry. Primary optical measurements indicated that the fluorescence of the ester form of this probe (4) could be selectively quenched by Pb(2+). In contrast, the fluorescence intensity of its analog 5 with released carboxylic groups was uniquely diminished by Cu(2+) with remarkably enhanced sensitivity and selectivity. Moreover, subsequent addition of cyanide to the methanol solution of the resulting Cu(2+)-5 complex induced its fluorescence recovery with a nanomolar detection limit, which was two orders of magnitude smaller than the regulated concentration limit of CN(-) in drinking water. This suggests the promising applicability of C-glycosyl bis-triazolyl amino acid scaffold in the future design and exploration of sensitive "off-on" Cu(II)-cyanide chemosensors.
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, PR China.
authors.forename: Yan-Hui
authors.initials: YH
authors.lastname: Tang
authors.forename: Yi
authors.initials: Y
authors.lastname: Qu
authors.forename: Zhuo
authors.initials: Z
authors.lastname: Song
authors.forename: Xiao-Peng
authors.initials: XP
authors.lastname: He
authors.forename: Juan
authors.initials: J
authors.lastname: Xie
authors.forename: Jianli
authors.initials: J
authors.lastname: Hua
authors.forename: Guo-Rong
authors.initials: GR
authors.lastname: Chen
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002623:Chemistry Techniques, Analytical / Q000295:instrumentation*; D003300:Copper / Q000737:chemistry*; D003486:Cyanides / Q000032:analysis* / Q000737:chemistry*; D006031:Glycosylation; D057230:Limit of Detection; D013050:Spectrometry, Fluorescence; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D003486:Cyanides; D014230:Triazoles; D003300:Copper