Recognition of Free Tryptophan in Water by Synthetic Pseudopeptides: Fluorescence and Thermodynamic Studies
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Otros documentos de la autoría: Martí-Centelles, Vicente; Izquierdo Arcusa, María Ángeles; Burguete, M. Isabel; Galindo, Francisco; Luis, Santiago V.
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http://dx.doi.org/10.1002/chem.201400346 |
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Título
Recognition of Free Tryptophan in Water by Synthetic Pseudopeptides: Fluorescence and Thermodynamic StudiesAutoría
Fecha de publicación
2014-06Editor
WILEY-VCH Verlag GmbH & Co. KGaAISSN
0947-6539; 1521-3765Tipo de documento
info:eu-repo/semantics/articleVersión de la editorial
http://onlinelibrary.wiley.com/doi/10.1002/chem.201304851/fullPalabras clave / Materias
Resumen
Pseudopeptidic receptors containing an acridine unit have been prepared and their fluorescence response to a series of amino acids was measured in water. Free amino acids, not protected either at the C or the N terminus, ... [+]
Pseudopeptidic receptors containing an acridine unit have been prepared and their fluorescence response to a series of amino acids was measured in water. Free amino acids, not protected either at the C or the N terminus, were used for this purpose. The prepared receptors display a selective response to tryptophan (Trp) versus the other assayed amino acids under acidic conditions. The macrocyclic nature of the receptor is important as the fluorescence quenching is higher for the macrocyclic compound than for the related open-chain receptor. Notably, under the experimental acidic conditions used, both the receptor and guest are fully protonated and positively charged; thus, the experimental results suggest the formation of supramolecular species that contain two positively charged organic molecular components in proximity stabilized through aromatic–aromatic interactions and a complex set of cation-anion-cation interactions. The selectivity towards Trp seems to be based on the existence of a strong association between the indole ring of the monocharged amino acid and the acridinium fragment of the triprotonated form of the receptor, which is established to be assisted by the interaction of the cationic moieties with hydrogen sulfate anions. [-]
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Chemistry - A European Journal Vol. 20, no. 24, 2014Derechos de acceso
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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