title: Synthesis of new trisulfonated calix[4]arenes functionalized at the upper rim, and their complexation with the trimethyllysine epigenetic mark.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Victoria, P.O. Box 3065, STN CSC, Victoria, BC, Canada.
authors.forename: Kevin D
authors.initials: KD
authors.lastname: Daze
authors.forename: Manuel C F
authors.initials: MC
authors.lastname: Ma
authors.forename: Florent
authors.initials: F
authors.lastname: Pineux
authors.forename: Fraser
authors.initials: F
authors.lastname: Hof
mesh_terms: D047250:Calixarenes / Q000138:chemical synthesis* / Q000737:chemistry; D008239:Lysine / Q000031:analogs & derivatives* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D013451:Sulfonic Acids / Q000737:chemistry*
chemical_list: D013451:Sulfonic Acids; D047250:Calixarenes; C003712:trimethyllysine; D008239:Lysine