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Issue 3, 2012
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Discovery of a sensitive Cu(ii)-cyanide “off–on” sensor based on new C-glycosyl triazolyl bis-amino acid scaffold

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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 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.

Graphical abstract: Discovery of a sensitive Cu(ii)-cyanide “off–on” sensor based on new C-glycosyl triazolyl bis-amino acid scaffold

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Article information


Submitted
24 Jul 2011
Accepted
19 Oct 2011
First published
20 Oct 2011

Org. Biomol. Chem., 2012,10, 555-560
Article type
Paper

Discovery of a sensitive Cu(II)-cyanide “off–on” sensor based on new C-glycosyl triazolyl bis-amino acid scaffold

Y. Tang, Y. Qu, Z. Song, X. He, J. Xie, J. Hua and G. Chen, Org. Biomol. Chem., 2012, 10, 555
DOI: 10.1039/C1OB06242E

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