Enantioseparation of -amino acids by means of Cinchona alkaloids asselectors 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 -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.
Fil: Keunchkarian, Sonia. Universidad Nacional de La Plata. División Química Analítica. Laboratorio de Investigación y Desarrollo de Métodos Analíticos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Franca, Carlos Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico La Plata. Centro de Química Inorgánica; Argentina
Fil: Gagliardi, Leonardo Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico La Plata. Centro de Investigación y Desarrollo en Tecnología de Pinturas (i); Argentina. Universidad Nacional de La Plata. División Química Analítica. Laboratorio de Investigación y Desarrollo de Métodos Analíticos; Argentina
Fil: Castells, Cecilia Beatriz Marta. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico La Plata. Centro de Investigación y Desarrollo en Tecnología de Pinturas (i); Argentina. Universidad Nacional de La Plata. División Química Analítica. Laboratorio de Investigación y Desarrollo de Métodos Analíticos; Argentina
Materia
Cinchona Alkaloids
Α-Amino Acids
Chiral Ligand-Exchange Chromatography
Semi-Empirical Force-field Methods
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/11174
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/11174
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Enantioseparation of -amino acids by means of Cinchona alkaloids asselectors in chiral ligand-exchange chromatographyKeunchkarian, SoniaFranca, Carlos AlbertoGagliardi, Leonardo GabrielCastells, Cecilia Beatriz MartaCinchona AlkaloidsΑ-Amino AcidsChiral Ligand-Exchange ChromatographySemi-Empirical Force-field Methodshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A conventional nonchiral column was used for the enantioseparation of several racemic -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.Fil: Keunchkarian, Sonia. Universidad Nacional de La Plata. División Química Analítica. Laboratorio de Investigación y Desarrollo de Métodos Analíticos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Franca, Carlos Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico La Plata. Centro de Química Inorgánica; ArgentinaFil: Gagliardi, Leonardo Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico La Plata. Centro de Investigación y Desarrollo en Tecnología de Pinturas (i); Argentina. Universidad Nacional de La Plata. División Química Analítica. Laboratorio de Investigación y Desarrollo de Métodos Analíticos; ArgentinaFil: Castells, Cecilia Beatriz Marta. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico La Plata. Centro de Investigación y Desarrollo en Tecnología de Pinturas (i); Argentina. Universidad Nacional de La Plata. División Química Analítica. Laboratorio de Investigación y Desarrollo de Métodos Analíticos; ArgentinaElsevier Science2013-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/11174Keunchkarian, Sonia; Franca, Carlos Alberto; Gagliardi, Leonardo Gabriel; Castells, Cecilia Beatriz Marta; Enantioseparation of -amino acids by means of Cinchona alkaloids asselectors in chiral ligand-exchange chromatography; Elsevier Science; Journal Of Chromatography - A; 1298; 7-2013; 103-1080021-9673enginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.chroma.2013.05.030info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0021967313007802info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:01:49Zoai:ri.conicet.gov.ar:11336/11174instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:01:49.386CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Enantioseparation of -amino acids by means of Cinchona alkaloids asselectors in chiral ligand-exchange chromatography
title Enantioseparation of -amino acids by means of Cinchona alkaloids asselectors in chiral ligand-exchange chromatography
spellingShingle Enantioseparation of -amino acids by means of Cinchona alkaloids asselectors in chiral ligand-exchange chromatography
Keunchkarian, Sonia
Cinchona Alkaloids
Α-Amino Acids
Chiral Ligand-Exchange Chromatography
Semi-Empirical Force-field Methods
title_short Enantioseparation of -amino acids by means of Cinchona alkaloids asselectors in chiral ligand-exchange chromatography
title_full Enantioseparation of -amino acids by means of Cinchona alkaloids asselectors in chiral ligand-exchange chromatography
title_fullStr Enantioseparation of -amino acids by means of Cinchona alkaloids asselectors in chiral ligand-exchange chromatography
title_full_unstemmed Enantioseparation of -amino acids by means of Cinchona alkaloids asselectors in chiral ligand-exchange chromatography
title_sort Enantioseparation of -amino acids by means of Cinchona alkaloids asselectors 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 Cinchona Alkaloids
Α-Amino Acids
Chiral Ligand-Exchange Chromatography
Semi-Empirical Force-field Methods
topic Cinchona Alkaloids
Α-Amino Acids
Chiral Ligand-Exchange Chromatography
Semi-Empirical Force-field Methods
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A conventional nonchiral column was used for the enantioseparation of several racemic -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.
Fil: Keunchkarian, Sonia. Universidad Nacional de La Plata. División Química Analítica. Laboratorio de Investigación y Desarrollo de Métodos Analíticos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Franca, Carlos Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico La Plata. Centro de Química Inorgánica; Argentina
Fil: Gagliardi, Leonardo Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico La Plata. Centro de Investigación y Desarrollo en Tecnología de Pinturas (i); Argentina. Universidad Nacional de La Plata. División Química Analítica. Laboratorio de Investigación y Desarrollo de Métodos Analíticos; Argentina
Fil: Castells, Cecilia Beatriz Marta. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico La Plata. Centro de Investigación y Desarrollo en Tecnología de Pinturas (i); Argentina. Universidad Nacional de La Plata. División Química Analítica. Laboratorio de Investigación y Desarrollo de Métodos Analíticos; Argentina
description A conventional nonchiral column was used for the enantioseparation of several racemic -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
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://hdl.handle.net/11336/11174
Keunchkarian, Sonia; Franca, Carlos Alberto; Gagliardi, Leonardo Gabriel; Castells, Cecilia Beatriz Marta; Enantioseparation of -amino acids by means of Cinchona alkaloids asselectors in chiral ligand-exchange chromatography; Elsevier Science; Journal Of Chromatography - A; 1298; 7-2013; 103-108
0021-9673
url http://hdl.handle.net/11336/11174
identifier_str_mv Keunchkarian, Sonia; Franca, Carlos Alberto; Gagliardi, Leonardo Gabriel; Castells, Cecilia Beatriz Marta; Enantioseparation of -amino acids by means of Cinchona alkaloids asselectors in chiral ligand-exchange chromatography; Elsevier Science; Journal Of Chromatography - A; 1298; 7-2013; 103-108
0021-9673
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.chroma.2013.05.030
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0021967313007802
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1844613816233492480
score 13.070432

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