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Glucose binding drives reconfiguration of a dynamic library of urea-containing metal–organic assemblies

Dong Yang, Larissa K. S. von Krbek, Le Yu, Tanya K. Ronson, John D. Thoburn, John P. Carpenter, Jake L. Greenfield, Duncan J. Howe, Biao Wu, Jonathan R. Nitschke*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A bis-urea-functionalized ditopic subcomponent assembled with 2-formylpyridine and FeII, resulting in a dynamic library of metal–organic assemblies: an irregular FeII4L6 structure and three FeII2L3 stereoisomers: left- and right-handed helicates and a meso-structure. This library reconfigured in response to the addition of monosaccharide derivatives, which served as guests for specific library members, and the rate of saccharide mutarotation was also enhanced by the library. The (P) enantiomer of the FeII2L3 helical structure bound β-D-glucose selectively over α-D-glucose. As a consequence, the library collapsed into the (P)-FeII2L3 helicate following glucose addition. The α-D-glucose was likewise transformed into the β-D-anomer during equilibration and binding. Thus, β-D-glucose and (P)-3 amplified each other in the product mixture, as metal–organic and saccharide libraries geared together into a single equilibrating system.

Original languageEnglish
Pages (from-to)4485-4490
Number of pages6
JournalAngewandte Chemie International Edition
Volume60
Issue number9
Early online date7 Jan 2021
DOIs
Publication statusPublished - 23 Feb 2021

Keywords

  • Dynamic combinatorial library
  • Glucose binding
  • Host–guest systems
  • Metal–organic assemblies
  • Supramolecular chemistry

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