Estudos de separação enantiosseletiva para uma série de sulfóxidos quirais em colunas poliméricas
Autor(a) principal: | |
---|---|
Data de Publicação: | 2010 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório Institucional da UFSCAR |
Texto Completo: | https://repositorio.ufscar.br/handle/ufscar/6458 |
Resumo: | The liquid chromatography enantiomeric separation of a series of seventeen chiral sulfoxides was systematically investigated using multimodal elution with the new synthetic polymeric stationary phases based on monomers N-(2- acryloylamino-(1R,2R)-cyclohexyl)-acrylamine (P-CAP®), N,N0-[(1R,2R)-1,2- diphenyl-1,2-ethanediyl]bis-2-propenamide (P-CAP-DP®) and trans-9,10-dihydro- 9,10-ethanoanthracene-(11S,12S)-11,12-dicarboxylic acid bis-4-vinylphenylamide (DEAVB). The sulfoxide series was composed of aryl alkyl sulfoxides, benzoimidazole sulfoxides and the drugs modafinil, albendazole sulfoxide, omeprazole, lansoprazole, pantoprazole and rabeprazole. This work examines the effectiveness of the polymeric chiral stationary phases for the separation of chiral sulfoxides and describes the superiority of DEABV for these separations in three different elution modes. The first ever reversed phase enantiomeric separations on these columns is demonstrated. Besides that, the use of non standard chromatography solvents was evaluated for the sulfoxides series on the polymeric stationary phases. The study of the development of polysaccharides chiral stationary phases (CSPs) immobilized on to aminopropilsilica was carried out using thermal or photochemical methods. The photochemical method was more effective and provided the production of a CSP based on amilose tris-3,5- dimethylphenylcarbamate (CSP 7). This column showed stability for non standards mobile phases; however, has showed low enantiorresolution power for the compounds investigated. Using the photochemical approach an amilose tris-3,5- dimetoxiphenylcarbamate (CSP 8) was also prepared. The immobilization conditions needs, however, futher investigations and these results will be also presented and discussed in this work. |
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Lourenço, Tiago de CamposCass, Quezia Bezerrahttp://genos.cnpq.br:12010/dwlattes/owa/prc_imp_cv_int?f_cod=K4781559E6http://lattes.cnpq.br/789943821362951369c59686-32f6-4abc-95f0-b7d66f5fb3262016-06-02T20:36:24Z2010-03-222016-06-02T20:36:24Z2010-03-12LOURENÇO, Tiago de Campos. Enantiomeric resolution of a chiral sulfoxide series by LC on synthetic polymeric columns with multimodal elution.. 2010. 131 f. Dissertação (Mestrado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2010.https://repositorio.ufscar.br/handle/ufscar/6458The liquid chromatography enantiomeric separation of a series of seventeen chiral sulfoxides was systematically investigated using multimodal elution with the new synthetic polymeric stationary phases based on monomers N-(2- acryloylamino-(1R,2R)-cyclohexyl)-acrylamine (P-CAP®), N,N0-[(1R,2R)-1,2- diphenyl-1,2-ethanediyl]bis-2-propenamide (P-CAP-DP®) and trans-9,10-dihydro- 9,10-ethanoanthracene-(11S,12S)-11,12-dicarboxylic acid bis-4-vinylphenylamide (DEAVB). The sulfoxide series was composed of aryl alkyl sulfoxides, benzoimidazole sulfoxides and the drugs modafinil, albendazole sulfoxide, omeprazole, lansoprazole, pantoprazole and rabeprazole. This work examines the effectiveness of the polymeric chiral stationary phases for the separation of chiral sulfoxides and describes the superiority of DEABV for these separations in three different elution modes. The first ever reversed phase enantiomeric separations on these columns is demonstrated. Besides that, the use of non standard chromatography solvents was evaluated for the sulfoxides series on the polymeric stationary phases. The study of the development of polysaccharides chiral stationary phases (CSPs) immobilized on to aminopropilsilica was carried out using thermal or photochemical methods. The photochemical method was more effective and provided the production of a CSP based on amilose tris-3,5- dimethylphenylcarbamate (CSP 7). This column showed stability for non standards mobile phases; however, has showed low enantiorresolution power for the compounds investigated. Using the photochemical approach an amilose tris-3,5- dimetoxiphenylcarbamate (CSP 8) was also prepared. The immobilization conditions needs, however, futher investigations and these results will be also presented and discussed in this work.Este trabalho descreve a investigação do poder de enantiorresolução de novas fases estacionária quirais (CSP) de polímero sintético preparadas a partir dos monômeros poli(trans-1,2-ciclohexanediil-bis acrilamida (P-CAP®), N,N´- [(1R,2R)-1,2-difenil-1,2-etanodil]bis-2-propenamida (P-CAP-DP®) e trans-9,10- dihidro-9,10-etanoantraceno-(11S,12S)-11,12-acido dicarboxilico bis-4-vinilfenilamida (DEAVB) para uma série de dezessete sulfóxidos quirais. A série de sulfóxidos composta por aril alquil sulfóxidos, sulfóxidos benzoimidazólicos e pelos fármacos quirais modafinil, albendazol sulfóxido, omeprazol, lansoprazol, pantoprazol e rabeprazol foram eluidos no modo multimodal. O estudo sistemático da eficiência das três colunas de polímero sintético na enantiorresolução da séries de sulfóxidos quirais e a superioridade da DEAVB nas separações destes compostos nos três diferentes modos de eluição são apresentados. A P-CAP®, P-CAP-DP® e DEAVB também foram avaliadas pela primeira vez no modo reverso de eluição e a estabilidade destas colunas foi investigada pelo uso de solventes cromatográficos não usuais. O estudo do desenvolvimento de fases estacionárias quirais de derivados de polissacarídeos imobilizados em sílica APS foi realizado utilizando-se métodos térmicos ou fotoquímicos. O método fotoquímico foi mais eficiente e proporcionou o preparo da coluna de tris-3,5-dimetilfenilcarbamato de amilose (CSP 7). Esta coluna apresentou estabilidade frente a solventes cromatográficos não usuais, porém demonstrou baixo poder de enantiorresolução para os compostos quirais avaliados. Através do procedimento fotoquímico a CSP de tris-3,5- dimetoxifenilcarbamato de amilose (CSP 8) também foi preparada. Todavia, as condições de imobilização necessitam de maiores investigações, estes resultados estão também presentes e discutidos neste trabalho.Universidade Federal de Minas Geraisapplication/pdfporUniversidade Federal de São CarlosPrograma de Pós-Graduação em Química - PPGQUFSCarBRAnálise cromatográficaCromatografia quiralColuna - cromatografiaColunas de polissacarídeosCIENCIAS EXATAS E DA TERRA::QUIMICAEstudos de separação enantiosseletiva para uma série de sulfóxidos quirais em colunas poliméricasEnantiomeric resolution of a chiral sulfoxide series by LC on synthetic polymeric columns with multimodal elution.info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesis-1-1867fc213-f339-49e1-a669-a1e54cf68bf1info:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFSCARinstname:Universidade Federal de São Carlos (UFSCAR)instacron:UFSCARORIGINAL2842.pdfapplication/pdf2590203https://repositorio.ufscar.br/bitstream/ufscar/6458/1/2842.pdfa6201fc3bbcdc0a7233f72991d0ef4b5MD51THUMBNAIL2842.pdf.jpg2842.pdf.jpgIM Thumbnailimage/jpeg9290https://repositorio.ufscar.br/bitstream/ufscar/6458/2/2842.pdf.jpg7073960325cb264c7ef0505c709c701dMD52ufscar/64582023-09-18 18:31:11.466oai:repositorio.ufscar.br:ufscar/6458Repositório InstitucionalPUBhttps://repositorio.ufscar.br/oai/requestopendoar:43222023-09-18T18:31:11Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)false |
dc.title.por.fl_str_mv |
Estudos de separação enantiosseletiva para uma série de sulfóxidos quirais em colunas poliméricas |
dc.title.alternative.eng.fl_str_mv |
Enantiomeric resolution of a chiral sulfoxide series by LC on synthetic polymeric columns with multimodal elution. |
title |
Estudos de separação enantiosseletiva para uma série de sulfóxidos quirais em colunas poliméricas |
spellingShingle |
Estudos de separação enantiosseletiva para uma série de sulfóxidos quirais em colunas poliméricas Lourenço, Tiago de Campos Análise cromatográfica Cromatografia quiral Coluna - cromatografia Colunas de polissacarídeos CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Estudos de separação enantiosseletiva para uma série de sulfóxidos quirais em colunas poliméricas |
title_full |
Estudos de separação enantiosseletiva para uma série de sulfóxidos quirais em colunas poliméricas |
title_fullStr |
Estudos de separação enantiosseletiva para uma série de sulfóxidos quirais em colunas poliméricas |
title_full_unstemmed |
Estudos de separação enantiosseletiva para uma série de sulfóxidos quirais em colunas poliméricas |
title_sort |
Estudos de separação enantiosseletiva para uma série de sulfóxidos quirais em colunas poliméricas |
author |
Lourenço, Tiago de Campos |
author_facet |
Lourenço, Tiago de Campos |
author_role |
author |
dc.contributor.authorlattes.por.fl_str_mv |
http://lattes.cnpq.br/7899438213629513 |
dc.contributor.author.fl_str_mv |
Lourenço, Tiago de Campos |
dc.contributor.advisor1.fl_str_mv |
Cass, Quezia Bezerra |
dc.contributor.advisor1Lattes.fl_str_mv |
http://genos.cnpq.br:12010/dwlattes/owa/prc_imp_cv_int?f_cod=K4781559E6 |
dc.contributor.authorID.fl_str_mv |
69c59686-32f6-4abc-95f0-b7d66f5fb326 |
contributor_str_mv |
Cass, Quezia Bezerra |
dc.subject.por.fl_str_mv |
Análise cromatográfica Cromatografia quiral Coluna - cromatografia Colunas de polissacarídeos |
topic |
Análise cromatográfica Cromatografia quiral Coluna - cromatografia Colunas de polissacarídeos CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The liquid chromatography enantiomeric separation of a series of seventeen chiral sulfoxides was systematically investigated using multimodal elution with the new synthetic polymeric stationary phases based on monomers N-(2- acryloylamino-(1R,2R)-cyclohexyl)-acrylamine (P-CAP®), N,N0-[(1R,2R)-1,2- diphenyl-1,2-ethanediyl]bis-2-propenamide (P-CAP-DP®) and trans-9,10-dihydro- 9,10-ethanoanthracene-(11S,12S)-11,12-dicarboxylic acid bis-4-vinylphenylamide (DEAVB). The sulfoxide series was composed of aryl alkyl sulfoxides, benzoimidazole sulfoxides and the drugs modafinil, albendazole sulfoxide, omeprazole, lansoprazole, pantoprazole and rabeprazole. This work examines the effectiveness of the polymeric chiral stationary phases for the separation of chiral sulfoxides and describes the superiority of DEABV for these separations in three different elution modes. The first ever reversed phase enantiomeric separations on these columns is demonstrated. Besides that, the use of non standard chromatography solvents was evaluated for the sulfoxides series on the polymeric stationary phases. The study of the development of polysaccharides chiral stationary phases (CSPs) immobilized on to aminopropilsilica was carried out using thermal or photochemical methods. The photochemical method was more effective and provided the production of a CSP based on amilose tris-3,5- dimethylphenylcarbamate (CSP 7). This column showed stability for non standards mobile phases; however, has showed low enantiorresolution power for the compounds investigated. Using the photochemical approach an amilose tris-3,5- dimetoxiphenylcarbamate (CSP 8) was also prepared. The immobilization conditions needs, however, futher investigations and these results will be also presented and discussed in this work. |
publishDate |
2010 |
dc.date.available.fl_str_mv |
2010-03-22 2016-06-02T20:36:24Z |
dc.date.issued.fl_str_mv |
2010-03-12 |
dc.date.accessioned.fl_str_mv |
2016-06-02T20:36:24Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
LOURENÇO, Tiago de Campos. Enantiomeric resolution of a chiral sulfoxide series by LC on synthetic polymeric columns with multimodal elution.. 2010. 131 f. Dissertação (Mestrado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2010. |
dc.identifier.uri.fl_str_mv |
https://repositorio.ufscar.br/handle/ufscar/6458 |
identifier_str_mv |
LOURENÇO, Tiago de Campos. Enantiomeric resolution of a chiral sulfoxide series by LC on synthetic polymeric columns with multimodal elution.. 2010. 131 f. Dissertação (Mestrado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2010. |
url |
https://repositorio.ufscar.br/handle/ufscar/6458 |
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por |
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info:eu-repo/semantics/openAccess |
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openAccess |
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application/pdf |
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Universidade Federal de São Carlos |
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Programa de Pós-Graduação em Química - PPGQ |
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UFSCar |
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BR |
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Universidade Federal de São Carlos |
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