Molecular Tweezers with Additional Recognition Sites

Chemistry : a European Journal
Christian HeidThomas Schrader

Abstract

A new synthetic access to molecular tweezers with one or two aliphatic phosphate ester groups in the central benzene spacer-unit is presented. Alkynyl ester groups offer the prospect to attach additional functional units by click chemistry and greatly broaden the scope of these tools for chemical biology. We present two alternative strategies: the trichloroacetonitrile method involves activation of only one OH group of each phosphoric acid substituent by way of trichloroacetimidate intermediates and subsequent introduction of an aliphatic ester alcohol moiety. The method is versatile, robust and combines simple workup with high yields. Mono- and disubstituted novel host structures are thus accessible in a convenient way. Alternatively, the phosphoramidite strategy activates the hydroquinone precursor by way of phosphoramidite intermediates and couples the desired ester alcohols followed by mild oxidation to the desired phosphate esters. Each step of the synthesis is carried out at very mild conditions and allows to combine sensitive host candidates and recognition elements. After neutralization of the phosphoric acids to water-soluble tri- and tetra-anions the cavities of the new tweezer derivatives are open to bind lysine and ...Continue Reading

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Citations

Aug 29, 2019·Chemical Communications : Chem Comm·Jimi M AlexPeter B Crowley
Jun 30, 2019·FEBS Letters·Sylvain EngilbergePeter B Crowley
May 30, 2019·Chemistry : a European Journal·Lei LiRoland Hermann Alfons Winter
Oct 22, 2019·Frontiers in Chemistry·Inesa HadrovicThomas Schrader
Oct 14, 2020·Chemistry : a European Journal·Hannah P Ferguson JohnsMarcey L Waters
Mar 10, 2021·Nature Communications·Annika MeinersShirley K Knauer
Mar 21, 2021·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Vikas KumarSebastian Schlücker
May 25, 2021·The Journal of Physical Chemistry. B·Oliver WetzelMatthias Epple
Aug 25, 2021·Journal of the American Chemical Society·Xavier GuilloryChristian Ottmann
Dec 29, 2020·The Journal of Physical Chemistry. B·Selina Beatrice van der MeerMatthias Epple

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