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Issue 28, 2017
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Exploring cucurbit[6]uril–peptide interactions in the solid state: crystal structure of cucurbit[6]uril complexes with glycyl-containing dipeptides

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Abstract

Macrocyclic host cucurbit[6]uril forms supramolecular complexes with dipeptides sequenced as Gly-X (X is either an aromatic amino acid residue Phe, Tyr, and Trp or Gly) in the solid state. Despite exclusion complexation, the interaction between guest dipeptide and host cucurbit[6]uril is multipoint. The ammonium and amide nitrogen atoms of dipeptide participate in hydrogen bonding with a host carbonyl rim and water molecules or chloride anions trapped inside the macrocyclic cavity. The structural study reveals the stabilizing role of the aromatic residues in the supramolecular assembly due to their complementarity with the outer surface of cucurbit[6]uril. In the absence of an aromatic side chain, the calcium ions can stabilize and guide the supramolecular assembly between the macrocycle and Gly-Gly dipeptide.

Graphical abstract: Exploring cucurbit[6]uril–peptide interactions in the solid state: crystal structure of cucurbit[6]uril complexes with glycyl-containing dipeptides

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Publication details

The article was received on 09 May 2017, accepted on 14 Jun 2017 and first published on 15 Jun 2017


Article type: Communication
DOI: 10.1039/C7CE00881C
Citation: CrystEngComm, 2017,19, 3892-3897
  • Open access: Creative Commons BY license
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    Exploring cucurbit[6]uril–peptide interactions in the solid state: crystal structure of cucurbit[6]uril complexes with glycyl-containing dipeptides

    O. Danylyuk, CrystEngComm, 2017, 19, 3892
    DOI: 10.1039/C7CE00881C

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