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Stereoselective recognition of the Ac-Glu-Tyr-OH dipeptide by pseudopeptidic cages
dc.contributor.author | Faggi, Enrico | |
dc.contributor.author | Vicent Barrera, Cristian | |
dc.contributor.author | Luis, Santiago V. | |
dc.contributor.author | Alfonso Rodríguez, Ignacio | |
dc.date.accessioned | 2016-05-05T15:52:48Z | |
dc.date.available | 2016-05-05T15:52:48Z | |
dc.date.issued | 2015 | |
dc.identifier.citation | Org. Biomol. Chem., 2015, 13, 11721 | ca_CA |
dc.identifier.issn | 1477-0520 | |
dc.identifier.issn | 1477-0539 | |
dc.identifier.uri | http://hdl.handle.net/10234/159319 | |
dc.description.abstract | Pseudopeptidic molecular cages are appealing receptors since they can display different polar and nonpolar interaction sites in a modular framework and a controlled disposition. Inspired by previous host– guest knowledge, two pseudopeptidic molecular cages based on serine and threonine (CySer and CyThr, respectively) were designed and synthesized as hosts for the binding of the four possible stereoisomers of the Ac-Glu-Tyr-OH dipeptide, a target sequence of tyrosine kinases. The careful NMR titration experiments in aqueous acetonitrile allowed the determination of the binding constants and reflected a difference in the stability of the corresponding diastereomeric host–guest complexes. The CySer cage proved to be slightly more efficient than the CyThr counterpart, although both showed similar stereoselectivity trends: LL > DD ≥ LD > DL. This stereoselective binding was retained in the gas phase, as shown by ESI-MS competition experiments using the enantiomer-labelled method (EL), as well as CID experiments. Thus, the MS-determined discriminations follow the same trends observed by NMR, suggesting that the stereoselectivity observed for these systems must be mainly dictated by the polar host–guest interactions. Despite the stereoselective binding of short peptide sequences in competitive media being a challenging issue in supramolecular chemistry, our results demonstrate the power of pseudopeptidic cages in molecular recognition with foreseen implications in chemical biology | ca_CA |
dc.description.sponsorShip | Spanish Ministry of Economy and Competitiveness (MINECO) CTQ2012-38543-C03. Generalitat de Catalunya (AGAUR) 2014 SGR 231. CSIC. European Social Fund. | ca_CA |
dc.format.extent | 11 p. | ca_CA |
dc.language.iso | eng | ca_CA |
dc.publisher | Royal Society of Chemistry | ca_CA |
dc.relation.isPartOf | Org. Biomol. Chem., 2015, 13, 11721–11731 | ca_CA |
dc.rights | "Reproduced by permission of The Royal Society of Chemistry" This journal is © The Royal Society of Chemistry 2015 | ca_CA |
dc.rights.uri | http://rightsstatements.org/vocab/InC/1.0/ | * |
dc.subject | chiral molecular recognition | ca_CA |
dc.subject | mass-spectrometric methods | ca_CA |
dc.subject | alanyl-d-alanine | ca_CA |
dc.subject | amino-acids | ca_CA |
dc.subject | electrospray-ionization | ca_CA |
dc.subject | synthetic receptor | ca_CA |
dc.subject | selective binding | ca_CA |
dc.subject | aqueous-solution | ca_CA |
dc.subject | gas-phase | ca_CA |
dc.subject | enantioselective recognition | ca_CA |
dc.title | Stereoselective recognition of the Ac-Glu-Tyr-OH dipeptide by pseudopeptidic cages | ca_CA |
dc.type | info:eu-repo/semantics/article | ca_CA |
dc.identifier.doi | http://dx.doi.org/10.1039/c5ob01889g | |
dc.rights.accessRights | info:eu-repo/semantics/restrictedAccess | ca_CA |
dc.relation.publisherVersion | http://pubs.rsc.org/en/content/articlelanding/2015/ob/c5ob01889g#!divAbstract | ca_CA |
dc.type.version | info:eu-repo/semantics/publishedVersion | ca_CA |
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