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

Autores
Keunchkarian, Sonia; Franca, Carlos Alberto; Gagliardi, Leonardo Gabriel; Castells, Cecilia Beatriz Marta
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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
Materia
Ciencias Exactas
Química
Cinchona alkaloids
α-Amino acids
Chiral ligand-exchange chromatography
Semi-empirical force-field methods
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by/4.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/151455
Acceder
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oai_identifier_str oai:sedici.unlp.edu.ar:10915/151455
network_acronym_str SEDICI
repository_id_str 1329
network_name_str SEDICI (UNLP)
spelling Enantioseparation of α-amino acids by means of Cinchona alkaloids as selectors in chiral ligand-exchange chromatographyKeunchkarian, SoniaFranca, Carlos AlbertoGagliardi, Leonardo GabrielCastells, Cecilia Beatriz MartaCiencias ExactasQuímicaCinchona alkaloidsα-Amino acidsChiral ligand-exchange chromatographySemi-empirical force-field methodsA 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 AnalíticosCentro de Química InorgánicaCentro de Investigación y Desarrollo en Tecnología de Pinturas2013-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf103-108http://sedici.unlp.edu.ar/handle/10915/151455enginfo:eu-repo/semantics/altIdentifier/issn/0021-9673info:eu-repo/semantics/altIdentifier/doi/10.1016/j.chroma.2013.05.030info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/Creative Commons Attribution 4.0 International (CC BY 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-10-22T17:19:57Zoai:sedici.unlp.edu.ar:10915/151455Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-10-22 17:19:57.356SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv Enantioseparation of α-amino acids by means of Cinchona alkaloids as selectors in chiral ligand-exchange chromatography
title Enantioseparation of α-amino acids by means of Cinchona alkaloids as selectors in chiral ligand-exchange chromatography
spellingShingle Enantioseparation of α-amino acids by means of Cinchona alkaloids as selectors in chiral ligand-exchange chromatography
Keunchkarian, Sonia
Ciencias Exactas
Química
Cinchona alkaloids
α-Amino acids
Chiral ligand-exchange chromatography
Semi-empirical force-field methods
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
dc.creator.none.fl_str_mv Keunchkarian, Sonia
Franca, Carlos Alberto
Gagliardi, Leonardo Gabriel
Castells, Cecilia Beatriz Marta
author Keunchkarian, Sonia
author_facet Keunchkarian, Sonia
Franca, Carlos Alberto
Gagliardi, Leonardo Gabriel
Castells, Cecilia Beatriz Marta
author_role author
author2 Franca, Carlos Alberto
Gagliardi, Leonardo Gabriel
Castells, Cecilia Beatriz Marta
author2_role author
author
author
dc.subject.none.fl_str_mv Ciencias Exactas
Química
Cinchona alkaloids
α-Amino acids
Chiral ligand-exchange chromatography
Semi-empirical force-field methods
topic Ciencias Exactas
Química
Cinchona alkaloids
α-Amino acids
Chiral ligand-exchange chromatography
Semi-empirical force-field methods
dc.description.none.fl_txt_mv 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
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.
publishDate 2013
dc.date.none.fl_str_mv 2013-07
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Articulo
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://sedici.unlp.edu.ar/handle/10915/151455
url http://sedici.unlp.edu.ar/handle/10915/151455
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/0021-9673
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.chroma.2013.05.030
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
dc.format.none.fl_str_mv application/pdf
103-108
dc.source.none.fl_str_mv reponame:SEDICI (UNLP)
instname:Universidad Nacional de La Plata
instacron:UNLP
reponame_str SEDICI (UNLP)
collection SEDICI (UNLP)
instname_str Universidad Nacional de La Plata
instacron_str UNLP
institution UNLP
repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
repository.mail.fl_str_mv alira@sedici.unlp.edu.ar
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score 12.982451

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