Stereoselective recognition of the Ac-Glu-Tyr-OH dipeptide by pseudopeptidic cages
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Other documents of the author: Faggi, Enrico; Vicent Barrera, Cristian; Luis, Santiago V.; Alfonso Rodríguez, Ignacio
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comunitat-uji-handle2:10234/7053
comunitat-uji-handle3:10234/8639
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Title
Stereoselective recognition of the Ac-Glu-Tyr-OH dipeptide by pseudopeptidic cagesDate
2015Publisher
Royal Society of ChemistryISSN
1477-0520; 1477-0539Bibliographic citation
Org. Biomol. Chem., 2015, 13, 11721Type
info:eu-repo/semantics/articleVersion
info:eu-repo/semantics/publishedVersionSubject
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 ... [+]
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 [-]
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