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
- Institución
- Universidad Nacional de La Plata
- OAI Identificador
- oai:sedici.unlp.edu.ar:10915/151455
Ver los metadatos del registro completo
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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:UNLP2025-09-29T11:39:01Zoai: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:13292025-09-29 11:39:01.825SEDICI (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 |
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Universidad Nacional de La Plata |
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UNLP |
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SEDICI (UNLP) - Universidad Nacional de La Plata |
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alira@sedici.unlp.edu.ar |
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