Molecular recognition of N-protected dipeptides by pseudopeptidic macrocycles: a comparative study of the supramolecular complexes by ESI-MS and NMR

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 intera...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2010-03, Vol.8 (6), p.1329-1339
Main Authors: Alfonso, Ignacio, Bolte, Michael, Bru, Miriam, Burguete, M Isabel, Luis, Santiago V, Vicent, Cristian
Format: Article
Language:English
Subjects:
Amides - chemistry
Dipeptides - chemistry
Dipeptides - metabolism
Gases - chemistry
Macrocyclic Compounds - metabolism
Magnetic Resonance Spectroscopy
Models, Molecular
Nitrogen - chemistry
Protein Binding
Protein Conformation
Protein Stability
Solutions
Spectrometry, Mass, Electrospray Ionization
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/b924981h