Synthesis of New Trisulfonated Calix[4]arenes Functionalized at the Upper Rim, and Their Complexation with the Trimethyllysine Epigenetic Mark

Kevin D. Daze, Fraser Hof, Manuel C. F. Ma & Florent Pineux
A synthetic route to produce a new family of trisulfonated calix[4]arenes bearing a single group, selectively introduced, that lines the binding pocket is reported. Ten examples, including new sulfonamide and biphenyl-substituted hosts, each with additional binding elements, demonstrate the tuning of guest affinities and selectivities. NMR titrations in phosphate-buffered water show that one of the new hosts binds to the modified amino acid trimethyllysine with the highest affinity and selectivity observed to date.
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