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Cucurbituril selectively binds the epigenetic mark Nε,Nε,Nε-trimethyllysine (LysMe3, KCB = (1.8 ± 0.6)× 106 dm3 mol−1) by 3500-fold over lysine ((5.3 ± 0.7) × 102 dm3 mol−1) in aqueous solution, using ion–dipole interactions and the hydrophobic effect, rather than cation–π interactions, as in the “aromatic cages” of p-SO3-calixarene hosts or chromodomain proteins which recognize LysMe3. The trend in KCB of LysMe3 > LysMe2 > LysMe > Lys follows the recognition pattern of the chromodomain HP1 and other LysMen protein readers. With CB, protonation of the guest carboxylate group is required for the formation of inclusion complexes with the LysMen series. The CB host also displays modest selectivity between the asymmetric ((2.0 ± 0.3) × 103 dm3 mol−1) and symmetric ((6.1 ± 0.6) × 103 dm3 mol−1) dimethylarginines, both of which bind more strongly than the parent arginine or monomethylarginine.
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Organic & Biomolecular Chemistry
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