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Discovery of a sensitive Cu(ii)-cyanide "off-on" sensor based on new C-glycosyl triazolyl bis-amino acid scaffold

Y.-H. Tang, Y. Qu, Z. Song, X.-P. He, J. Xie, J. Hua and G.-R. Chen Org. Biomol. Chem., 2012, 10, 3, 555-560

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 Pb2+. In contrast, the fluorescence intensity of its analog 5 with released carboxylic groups was uniquely diminished by Cu2+ with remarkably enhanced sensitivity and selectivity. Moreover, subsequent addition of cyanide to the methanol solution of the resulting Cu2+-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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Publication

Dates :

Paru le 9 janvier 2012

Informations complémentaires :

doi : 10.1039/C1OB06242E