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Issue 24, 2004
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A tong-like fluorescence sensor for metal ions: perfect conformational switch of hinge sugar by pyrene stacking

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Abstract

Carbohydrates are among the potential materials for molecular devices, since they are abundant natural resources. However, their rigidity has restricted their use for movable devices. Hinge sugars, 2,4-diamino-2,4-dideoxy-xylopyranosides, shed light on the use of carbohydrates as movable components, as demonstrated by the motion by which all four equatorial substituents can change to an axial orientation in synchronization with a chelation-driven 4C11C4 ring flip. In this study, we synthesized a tong-like metal ion sensor, 1,3-di-O-pyrenylmethylated hinge sugar (1), and its model compound, methyl 2,4-di-O-pyrenecarbonyl-xylopyranoside (2), to extend the abilities of hinge sugars as molecular components. From observations of the solvent-dependent conformational and fluorescent behavior of 2, we found that the pyrene stacking assists the 1C4 formation of xylopyranoside by 1.7 kcal mol−1. We also found that compound 1 produced excimer fluorescence by chelation to Pt2+, Zn2+, Cd2+, Mg2+ or Mn2+, and unexpectedly by addition of acids. 1H NMR measurements ascribed this behavior to the 4C11C4 ring flip of hinge sugar in response to chelation or protonation at N2, and revealed rapid and perfect 1C4 formation in the case of Zn2+. These findings will extend the scope of hinge sugars as movable components.

Graphical abstract: A tong-like fluorescence sensor for metal ions: perfect conformational switch of hinge sugar by pyrene stacking

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Publication details

The article was received on 26 Jul 2004, accepted on 11 Oct 2004 and first published on 18 Nov 2004


Article type: Paper
DOI: 10.1039/B411344F
Citation: Org. Biomol. Chem., 2004,2, 3548-3556

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    A tong-like fluorescence sensor for metal ions: perfect conformational switch of hinge sugar by pyrene stacking

    H. Yuasa, N. Miyagawa, M. Nakatani, M. Izumi and H. Hashimoto, Org. Biomol. Chem., 2004, 2, 3548
    DOI: 10.1039/B411344F

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