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Stereochemical Behavior of Pyrrolo-Pyrazole Peptidomimetics Promoting Phase-Selective Supramolecular Organogels.

Enrica ChiesaFrancesco AnastasiFrancesca ClericiEdoardo Mario LuminaIda GentaSara PellegrinoMaria Luisa Gelmi
Published in: Gels (Basel, Switzerland) (2024)
Supramolecular gels were developed by taking advantage of an assembly of small dipeptides containing pyrrolo-pyrazole scaffolds. The dipeptides were prepared through a robust and ecofriendly synthetic approach from the commercially available starting materials of diazoalkanes and maleimides. By playing with the functionalization of the scaffold, the choice of the natural amino acid, and the stereochemistry, we were able to obtain phase-selective gels. In particular, one peptidomimetic showed gelation ability and thermoreversibility in aromatic solvents at very low concentrations. Rheology tests showed a typical viscoelastic solid profile, indicating the formation of strong gels that were stable under high mechanical deformation. NMR studies were performed, allowing us to determine the conformational and stereochemical features at the base of the supramolecular interactions.
Keyphrases
  • amino acid
  • molecular docking
  • water soluble
  • energy transfer
  • tissue engineering
  • molecular dynamics simulations
  • magnetic resonance
  • molecular dynamics
  • high resolution
  • single molecule
  • case control
  • quantum dots