Nuclear magnetic resonance to study the interacions acting in the enantiomeric separation of homocysteine by capillary electrophoresis with a dual system of γ-cyclodextrin and (R)-N,N,N-trimethyl-2-aminobutanol-bis(trifluoromethanesulfon)imidate
Authors
Marina Alegre, María Luisa; Castro Puyana, María; Greño Ocariz, Maider; Salgado Serrano, AntonioIdentifiers
Permanent link (URI): http://hdl.handle.net/10017/39846DOI: 10.1002/elps.201800483
ISSN: 0173-0835
Date
2019-08Embargo end date
2020-09-01Affiliation
Universidad de Alcalá. Departamento de Química Analítica, Química Física e Ingeniería Química; Universidad de Alcalá. Departamento de Química Orgánica y Química InorgánicaBibliographic citation
Electrophoresis, 2019, v. 40, n. 15, p. 1913-1920
Keywords
Capillary electrophoresis
NMR
chiral ionic liquids
homocysteine
Description / Notes
doi: 10.1002/elps.201800483.
Project
CTQ2016-76368-P (Spanish Ministry of Economy and Competitiveness)
Document type
info:eu-repo/semantics/article
Version
info:eu-repo/semantics/publishedVersion
Rights
Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)
© Wiley-VCH
Access rights
info:eu-repo/semantics/openAccess
Abstract
The enantiomeric separation of FMOC-homocysteine by CE was investigated using γ-CD and the chiral ionic liquid (R)-N,N,N-trimethyl-2-aminobutanol- bis(trifluoromethane-sulfon)imidate (EtCholNTf2) as chiral selectors in a 50 mM borate buffer at pH 9.0. The separation of the enantiomers was achieved in 5 min with a resolution value of 0.9 when using 10 mM γ-CD. However, the enantiomeric separation did not take place when the ionic liquid was employed as sole the chiral selector. Thus, the combination of both selectors was studied, obtaining higher Rs values for FMOC-homocysteine and a reversal in the enantiomer migration order in comparison with the use of γ-CD alone in the separation buffer. Then, NMR experiments were carried out in order to explain the experimental results obtained. The NMR analyses showed the formation of an inclusion complex, being the hydrophobic group of FMOC-homocysteine inserted into the γ-CD cavity. Interactions between EtCholNTf2 and γ-CD were also observed, suggesting that the ionic liquid would also enter the cavity of the γ-CD.
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