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  • Title: Discovery of a sensitive Cu(II)-cyanide "off-on" sensor based on new C-glycosyl triazolyl bis-amino acid scaffold.
    Author: Tang YH, Qu Y, Song Z, He XP, Xie J, Hua J, Chen GR.
    Journal: Org Biomol Chem; 2012 Jan 21; 10(3):555-60. PubMed ID: 22101917.
    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.
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