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Glucose Binding Drives Reconfiguration of a Dynamic Library of Urea‐Containing Metal–Organic Assemblies
Author(s) -
Yang Dong,
Krbek Larissa K. S.,
Yu Le,
Ronson Tanya K.,
Thoburn John D.,
Carpenter John P.,
Greenfield Jake L.,
Howe Duncan J.,
Wu Biao,
Nitschke Jonathan R.
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202014568
Subject(s) - chemistry , monosaccharide , urea , mutarotation , metal , enantiomer , stereochemistry , anomer , combinatorial chemistry , organic chemistry
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 II 4 L 6 structure and three Fe II 2 L 3 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 II 2 L 3 helical structure bound β‐D‐glucose selectively over α‐D‐glucose. As a consequence, the library collapsed into the ( P )‐Fe II 2 L 3 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.