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Title: Interactions between glycyl-L-phenylalanine and β-cyclodextrin from diffusion, spectroscopic and computational studies
Authors: Ramos, M. L. 
Dias, D. C.
Justino, L. L. G. 
Verissimo, L. M. P. 
Valente, A. J. M. 
Esteso, M. A. 
Ribeiro, A. C. F. 
Leaist, D. G. 
Pina, J. 
Cabral, A. M. T. D. P. V.
Rodrigo, M. M.
Keywords: β-Cyclodextrin; Glycyl-L-phenylalanine; Dipeptide; Host-guest interaction; Binding constant
Issue Date: 1-Oct-2020
Publisher: Elsevier
Project: info:eu-repo/grantAgreement/FCT/UID/QUI/UI0313/2020 
Serial title, monograph or event: Journal of Molecular Liquids
Volume: 315
Abstract: The transport and association of the dipeptide glycyl-L-phenylalanine (Gly-L-Phen) in solutions containing cyclodextrins are of prime importance given its relevance in different areas, from biochemistry to wastewater treatment. We have investigated the interaction between aqueous Gly-L-Phen and β-cyclodextrin (β-CD) by NMR, DFT calculations in parallel with UV/visible absorption, luminescence spectral measurements and diffusion experiments. Ternary mutual diffusion coefficients of aqueous {Gly-L-Phen + β-CD} solutions have been measured by using the Taylor dispersion technique. The results show that the association of Gly-L-Phen and β-CD has a significant effect on the diffusion coefficients, consistent with an association constant of about 50 to 100, assuming a 1:1 (Gly-L-Phen):(β-CD) stoichiometry. This stoichiometry has been assessed by the continuous variation (Job's plot) method and the association constant was determined by using the Hildebrand-Benesi equation modified for NMR applications. The association constant was estimated to be equal to 40. This association constant is in close agreement with that obtained by fluorescence measurements (K = 43). Additionally, from NMR, detailed structural information on the complex has been obtained. This has been complemented by DFT and TD-DFT studies.
ISSN: 01677322
DOI: 10.1016/j.molliq.2020.113704
Rights: embargoedAccess
Appears in Collections:I&D CQC - Artigos em Revistas Internacionais

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