A Modular Phosphorylated Glycoluril‐Derived Molecular Tweezer for Potent Binding of Aliphatic Diamines
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 4527797
Author(s) Heilmann, Michael; Tiefenbacher, Konrad
Author(s) at UniBasel Heilmann, Michael
Tiefenbacher, Konrad Karl
Year 2019
Year: comment 2019
Title A Modular Phosphorylated Glycoluril‐Derived Molecular Tweezer for Potent Binding of Aliphatic Diamines
Journal Chem. Eur. J.
Volume 25
Pages / Article-Number 12900-12904
Abstract

Amolecular tweezerbasedon aglycoluril-de-rivedframeworkbearingfourphosphategroupswas syn-thesizedandshownto be capableof bindingorganicaminesin aqueous solution.This workreportstheKavaluesfor 30 complexes of this molecular tweezerandamineguests,determined by meansof1HNMR titrations.Boththe hydrophobiccavityandthe phosphategroupscontributeto the binding.Bulkiermolecules andmole-culesbearing negativelychargedgroupslike carboxylatesin aminoacidsbindless tightlydue to astericclashandcoulombicrepulsion. Thenarrowcavityandthe strongionicinteractionsof the phosphategroupswithammoni-um guestsfavorbindingofaliphatic diamines.Thesebind-ing propertiesclearlydistinguishthis systemfromstruc-turallyrelatedmolecular clipsand tweezers

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Digital Object Identifier DOI doi.org/10.1002/chem.201902556
   

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