Related Experiment Video
Updated: Jun 15, 2026
Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities
Published on: October 2, 2018
Molecular recognition of N-protected dipeptides by pseudopeptidic macrocycles: a comparative study of the
Ignacio Alfonso1, Michael Bolte, Miriam Bru
1Departamento de Química Biológica y Modelización Molecular, Instituto de Química Avanzada de Cataluña, Consejo Superior de Investigaciones Científicas, IQAC/CSIC, C/Jordi Girona18-26, E-08034, Barcelona, Spain. ignacio.alfonso@iqac.csic.es
Abstract:
The molecular recognition properties of pseudopeptidic macrocycles have been studied by ESI-MS and NMR spectroscopy, as highly complementary experimental techniques in solution and in the gas phase. We used ESI-MS competition experiments for the high throughput screening of the supramolecular interaction between four macrocyclic receptors and different peptide-like substrates in solution, rendering the best-fitted host-guest pairs. Further insights on the non-covalent recognition process in the gas-phase were obtained through collision induced dissociation (CID) experiments. Solution studies using NMR spectroscopy ((1)H NMR titrations, NOESY and DOSY) were carried out to prove the validity of ESI-MS as a high-throughput screening method for studying the molecular recognition of the investigated pseudopeptidic macrocycles. A clear selectivity for N-protected dipeptides over N-protected amino acids, and a slight preference for dipeptides bearing aromatic side chains were observed. On the basis of the results obtained from this approach, a mode of binding has been proposed.
