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

doi:10.1002/anie.202014568

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 journal › Article › peer-review

33 Citations (Scopus)

Abstract

A bis-urea-functionalized ditopic subcomponent assembled with 2-formylpyridine and Fe^II, resulting in a dynamic library of metal–organic assemblies: an irregular Fe^II₄L₆ structure and three Fe^II₂L₃ 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 Fe^II₂L₃ helical structure bound β-D-glucose selectively over α-D-glucose. As a consequence, the library collapsed into the (P)-Fe^II₂L₃ 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 language	English
Pages (from-to)	4485-4490
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	9
DOIs	https://doi.org/10.1002/anie.202014568
Publication status	Published - 23 Feb 2021
Externally published	Yes

Keywords

dynamic combinatorial library
glucose binding
host–guest systems
metal–organic assemblies
supramolecular chemistry

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10.1002/anie.202014568

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title = "Glucose Binding Drives Reconfiguration of a Dynamic Library of Urea-Containing Metal–Organic Assemblies",

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.",

keywords = "dynamic combinatorial library, glucose binding, host–guest systems, metal–organic assemblies, supramolecular chemistry",

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

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year = "2021",

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doi = "10.1002/anie.202014568",

language = "English",

volume = "60",

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journal = "Angewandte Chemie - International Edition",

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AU - von Krbek, Larissa K.S.

AU - Yu, Le

AU - Ronson, Tanya K.

AU - Thoburn, John D.

AU - Carpenter, John P.

AU - Greenfield, Jake L.

AU - Howe, Duncan J.

AU - Wu, Biao

AU - Nitschke, Jonathan R.

PY - 2021/2/23

Y1 - 2021/2/23

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AB - 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.

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Glucose Binding Drives Reconfiguration of a Dynamic Library of Urea-Containing Metal–Organic Assemblies

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