Selective molecular recognition of methylated lysines and arginines by cucurbit[6]uril and cucurbit[7]uril in aqueous solution

Org Biomol Chem. 2013 Jan 21;11(3):488-95. doi: 10.1039/c2ob27007b. Epub 2012 Nov 30.

Abstract

Cucurbit[7]uril selectively binds the epigenetic mark N(ε),N(ε),N(ε)-trimethyllysine (LysMe(3), K(CB[7]) = (1.8 ± 0.6)× 10(6) dm(3) mol(-1)) by 3500-fold over lysine ((5.3 ± 0.7) × 10(2) dm(3) 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-SO(3)-calix[4]arene hosts or chromodomain proteins which recognize LysMe(3). The trend in K(CB[7]) of LysMe(3) > LysMe(2) > LysMe > Lys follows the recognition pattern of the chromodomain HP1 and other LysMe(n) protein readers. With CB[6], protonation of the guest carboxylate group is required for the formation of inclusion complexes with the LysMe(n) series. The CB[7] host also displays modest selectivity between the asymmetric ((2.0 ± 0.3) × 10(3) dm(3) mol(-1)) and symmetric ((6.1 ± 0.6) × 10(3) dm(3) mol(-1)) dimethylarginines, both of which bind more strongly than the parent arginine or monomethylarginine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arginine / chemistry*
  • Bridged-Ring Compounds / chemistry*
  • Imidazoles / chemistry*
  • Lysine / chemistry*
  • Methylation
  • Molecular Structure
  • Solutions
  • Water / chemistry

Substances

  • Bridged-Ring Compounds
  • Imidazoles
  • Solutions
  • cucurbit(7)uril
  • Water
  • cucurbit(6)uril
  • Arginine
  • Lysine