Enantioseparation of α-amino acids by means of Cinchona alkaloids as selectors in chiral ligand-exchange chromatography

A conventional nonchiral column was used for the enantioseparation of several racemic a-amino acids (native and derivatized) through the use of Cinchona alkaloids as chiral selectors along with Cu(II) ions in chiral ligand-exchange chromatography. The mobile phase composition (i.e., the organic modi...

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Autores principales: Keunchkarian, Sonia, Franca, Carlos Alberto, Gagliardi, Leonardo Gabriel, Castells, Cecilia Beatriz Marta
Formato: Articulo
Lenguaje:Inglés
Publicado: 2013
Materias:
Ciencias Exactas
Química
Cinchona alkaloids
α-Amino acids
Chiral ligand-exchange chromatography
Semi-empirical force-field methods
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/151455
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-151455
record_format dspace
spelling I19-R120-10915-1514552023-04-13T20:40:26Z http://sedici.unlp.edu.ar/handle/10915/151455 issn:0021-9673 Enantioseparation of α-amino acids by means of Cinchona alkaloids as selectors in chiral ligand-exchange chromatography Keunchkarian, Sonia Franca, Carlos Alberto Gagliardi, Leonardo Gabriel Castells, Cecilia Beatriz Marta 2013-07 2023-04-13T19:04:13Z en Ciencias Exactas Química Cinchona alkaloids α-Amino acids Chiral ligand-exchange chromatography Semi-empirical force-field methods A conventional nonchiral column was used for the enantioseparation of several racemic a-amino acids (native and derivatized) through the use of Cinchona alkaloids as chiral selectors along with Cu(II) ions in chiral ligand-exchange chromatography. The mobile phase composition (i.e., the organic modifier content and pH) was studied in order to modulate retention and enantioselectivity. Good enantioseparation of many amino acids was obtained using equimolar amounts of Cu(II) and either cinchonidine, quinine or quinidine as chiral selectors in the mobile phase. The molecular geometry of the diastereomeric complexes formed was modeled and energetic differences between both compounds were calculated by methods based on semi-empirical force-field. Good correlations were obtained between experimental enantioselectivity factors and calculated energetic differences. Laboratorio de Investigación y Desarrollo de Métodos Analíticos Centro de Química Inorgánica Centro de Investigación y Desarrollo en Tecnología de Pinturas Articulo Articulo http://creativecommons.org/licenses/by/4.0/ Creative Commons Attribution 4.0 International (CC BY 4.0) application/pdf 103-108
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Ciencias Exactas
Química
Cinchona alkaloids
α-Amino acids
Chiral ligand-exchange chromatography
Semi-empirical force-field methods
spellingShingle Ciencias Exactas
Química
Cinchona alkaloids
α-Amino acids
Chiral ligand-exchange chromatography
Semi-empirical force-field methods
Keunchkarian, Sonia
Franca, Carlos Alberto
Gagliardi, Leonardo Gabriel
Castells, Cecilia Beatriz Marta
Enantioseparation of α-amino acids by means of Cinchona alkaloids as selectors in chiral ligand-exchange chromatography
topic_facet Ciencias Exactas
Química
Cinchona alkaloids
α-Amino acids
Chiral ligand-exchange chromatography
Semi-empirical force-field methods
description A conventional nonchiral column was used for the enantioseparation of several racemic a-amino acids (native and derivatized) through the use of Cinchona alkaloids as chiral selectors along with Cu(II) ions in chiral ligand-exchange chromatography. The mobile phase composition (i.e., the organic modifier content and pH) was studied in order to modulate retention and enantioselectivity. Good enantioseparation of many amino acids was obtained using equimolar amounts of Cu(II) and either cinchonidine, quinine or quinidine as chiral selectors in the mobile phase. The molecular geometry of the diastereomeric complexes formed was modeled and energetic differences between both compounds were calculated by methods based on semi-empirical force-field. Good correlations were obtained between experimental enantioselectivity factors and calculated energetic differences.
format Articulo
Articulo
author Keunchkarian, Sonia
Franca, Carlos Alberto
Gagliardi, Leonardo Gabriel
Castells, Cecilia Beatriz Marta
author_facet Keunchkarian, Sonia
Franca, Carlos Alberto
Gagliardi, Leonardo Gabriel
Castells, Cecilia Beatriz Marta
author_sort Keunchkarian, Sonia
title Enantioseparation of α-amino acids by means of Cinchona alkaloids as selectors in chiral ligand-exchange chromatography
title_short Enantioseparation of α-amino acids by means of Cinchona alkaloids as selectors in chiral ligand-exchange chromatography
title_full Enantioseparation of α-amino acids by means of Cinchona alkaloids as selectors in chiral ligand-exchange chromatography
title_fullStr Enantioseparation of α-amino acids by means of Cinchona alkaloids as selectors in chiral ligand-exchange chromatography
title_full_unstemmed Enantioseparation of α-amino acids by means of Cinchona alkaloids as selectors in chiral ligand-exchange chromatography
title_sort enantioseparation of α-amino acids by means of cinchona alkaloids as selectors in chiral ligand-exchange chromatography
publishDate 2013
url http://sedici.unlp.edu.ar/handle/10915/151455
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AT gagliardileonardogabriel enantioseparationofaaminoacidsbymeansofcinchonaalkaloidsasselectorsinchiralligandexchangechromatography
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