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Molecular recognition of N-protected dipeptides by pseudopeptidic macrocycles: a comparative study of the supramolecular complexes by ESI-MS and NMR
dc.contributor.author | Alfonso Rodríguez, Ignacio | |
dc.contributor.author | Bolte, Michael | |
dc.contributor.author | Burguete, M. Isabel | |
dc.contributor.author | Bru Roig, Miriam | |
dc.contributor.author | Luis, Santiago V. | |
dc.contributor.author | Vicent Barrera, Cristian | |
dc.date.accessioned | 2012-12-03T15:36:52Z | |
dc.date.available | 2012-12-03T15:36:52Z | |
dc.date.issued | 2010 | |
dc.identifier.citation | Organic & Biomolecular Chemistry (2010), 8, 6, p. 1329-1339 | ca_CA |
dc.identifier.issn | 1477-0520 | |
dc.identifier.uri | http://hdl.handle.net/10234/52701 | |
dc.description.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 (1H 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. | ca_CA |
dc.format.extent | 10 p. | ca_CA |
dc.language.iso | eng | ca_CA |
dc.publisher | Royal Society of Chemistry | ca_CA |
dc.rights | This journal is © The Royal Society of Chemistry 2010 | ca_CA |
dc.rights.uri | http://rightsstatements.org/vocab/InC/1.0/ | * |
dc.title | Molecular recognition of N-protected dipeptides by pseudopeptidic macrocycles: a comparative study of the supramolecular complexes by ESI-MS and NMR | ca_CA |
dc.type | info:eu-repo/semantics/article | ca_CA |
dc.identifier.doi | http://dx.doi.org/10.1039/B924981H | |
dc.rights.accessRights | info:eu-repo/semantics/closedAccess | ca_CA |
dc.relation.publisherVersion | http://pubs.rsc.org/en/content/articlelanding/2010/ob/b924981h | ca_CA |
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