Publicação
Separation of Nadolol Stereoisomers by Fixed-Bed and Continuous Preparative Liquid Chromatography using C18 Columns
| Resumo: | Continuous preparative liquid chromatography is nowadays a well-established technology used for the separation of a wide range of chemical mixtures. Among theseContinuous preparative liquid chromatography is nowadays a well-established technology used for the separation of a wide range of chemical mixtures. Among these techniques, the simulated moving bed (SMB) technology has gained an increasing interest to the industry in the production of fine chemicals and pharmaceuticals. This growing is due to the development of new and more versatile stationary phases, as well as new operating schemes for SMB and other continuous chromatographic processes. In recent years, the authors have focused in the preparative separation of chemical drugs by chiral SMB chromatography. Different case studies have been considered, including the separation of non-steroidal anti-inflammatory drugs (ketoprofen and flurbiprofen enantiomers) [1-4], and the pseudo-binary separation of nadolol stereoisomers, a beta-blocker pharmaceutical drug [5]. While the first two case studies are typical examples of binary chiral mixtures (a pair of enantiomers), the last is an example of a quaternary mixture, composed by two pairs of enantiomers. This considerably increases the complexity and the difficulty of the separation process, asking for new strategies for the complete resolution of all the four components. Experimental and simulation results have been recently presented considering a first step of a pseudo-binary separation by SMB (the more retained component being obtained pure in the extract and the other three co-eluting in the raffinate), followed by a ternary separation through a JO process [6]. This work introduces a different strategy using an achiral C18 stationary phase under reversed-phase mode to perform a first SMB separation step. The C18 achiral adsorbent allows the separation of the two pairs of nadolol diastereomers, i.e., the first racemate (composed by the nadolol compounds 2 and 3) co-eluting in the raffinate, and the second racemate (composed by the nadolol compounds 1 and 4) to be obtained in the extract SMB stream. After this preliminary achiral separation step, two parallel SMB runs must be carried out using a chiral stationary phase to achieve the complete separation of all the four nadolol stereoisomers. |
|---|---|
| Autores principais: | Ribeiro, António E. |
| Outros Autores: | Arafah, Rami; Rodrigues, Alírio; Pais, Luís S. |
| Assunto: | Continuous preparative liquid chromatography Simulated moving bed |
| Ano: | 2016 |
| País: | Portugal |
| Tipo de documento: | documento de conferência |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Instituto Politécnico de Bragança |
| Idioma: | inglês |
| Origem: | Biblioteca Digital do IPB |
| _version_ | 1867173173141700608 |
|---|---|
| author | Ribeiro, António E. |
| author2 | Arafah, Rami Rodrigues, Alírio Pais, Luís S. |
| author2_role | author author author |
| author_facet | Ribeiro, António E. Arafah, Rami Rodrigues, Alírio Pais, Luís S. |
| author_role | author |
| contributor_name_str_mv | Biblioteca Digital do IPB |
| country_str | PT |
| creators_json_txt | [{\"Person.name\":\"Ribeiro, António E.\",\"Person.identifier.orcid\":\"0000-0003-4569-7887\"},{\"Person.name\":\"Arafah, Rami\",\"Person.identifier.orcid\":\"0000-0002-7743-4988\"},{\"Person.name\":\"Rodrigues, Alírio\"},{\"Person.name\":\"Pais, Luís S.\",\"Person.identifier.orcid\":\"0000-0002-3000-2862\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | Biblioteca Digital do IPB |
| datacite.creators.creator.creatorName.fl_str_mv | Ribeiro, António E. Arafah, Rami Rodrigues, Alírio Pais, Luís S. |
| datacite.date.Accepted.fl_str_mv | 2016-01-01T00:00:00Z |
| datacite.date.available.fl_str_mv | 2018-03-19T14:57:40Z |
| datacite.date.embargoed.fl_str_mv | 2018-03-19T14:57:40Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | Continuous preparative liquid chromatography Simulated moving bed |
| datacite.titles.title.fl_str_mv | Separation of Nadolol Stereoisomers by Fixed-Bed and Continuous Preparative Liquid Chromatography using C18 Columns |
| dc.contributor.none.fl_str_mv | Biblioteca Digital do IPB |
| dc.creator.none.fl_str_mv | Ribeiro, António E. Arafah, Rami Rodrigues, Alírio Pais, Luís S. |
| dc.date.Accepted.fl_str_mv | 2016-01-01T00:00:00Z |
| dc.date.available.fl_str_mv | 2018-03-19T14:57:40Z |
| dc.date.embargoed.fl_str_mv | 2018-03-19T14:57:40Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | http://hdl.handle.net/10198/16374 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | FCUL |
| dc.rights.cclincense.fl_str_mv | http://creativecommons.org/licenses/by/4.0/ |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.subject.none.fl_str_mv | Continuous preparative liquid chromatography Simulated moving bed |
| dc.title.fl_str_mv | Separation of Nadolol Stereoisomers by Fixed-Bed and Continuous Preparative Liquid Chromatography using C18 Columns |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_c94f |
| description | Continuous preparative liquid chromatography is nowadays a well-established technology used for the separation of a wide range of chemical mixtures. Among theseContinuous preparative liquid chromatography is nowadays a well-established technology used for the separation of a wide range of chemical mixtures. Among these techniques, the simulated moving bed (SMB) technology has gained an increasing interest to the industry in the production of fine chemicals and pharmaceuticals. This growing is due to the development of new and more versatile stationary phases, as well as new operating schemes for SMB and other continuous chromatographic processes. In recent years, the authors have focused in the preparative separation of chemical drugs by chiral SMB chromatography. Different case studies have been considered, including the separation of non-steroidal anti-inflammatory drugs (ketoprofen and flurbiprofen enantiomers) [1-4], and the pseudo-binary separation of nadolol stereoisomers, a beta-blocker pharmaceutical drug [5]. While the first two case studies are typical examples of binary chiral mixtures (a pair of enantiomers), the last is an example of a quaternary mixture, composed by two pairs of enantiomers. This considerably increases the complexity and the difficulty of the separation process, asking for new strategies for the complete resolution of all the four components. Experimental and simulation results have been recently presented considering a first step of a pseudo-binary separation by SMB (the more retained component being obtained pure in the extract and the other three co-eluting in the raffinate), followed by a ternary separation through a JO process [6]. This work introduces a different strategy using an achiral C18 stationary phase under reversed-phase mode to perform a first SMB separation step. The C18 achiral adsorbent allows the separation of the two pairs of nadolol diastereomers, i.e., the first racemate (composed by the nadolol compounds 2 and 3) co-eluting in the raffinate, and the second racemate (composed by the nadolol compounds 1 and 4) to be obtained in the extract SMB stream. After this preliminary achiral separation step, two parallel SMB runs must be carried out using a chiral stationary phase to achieve the complete separation of all the four nadolol stereoisomers. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | conferenceObject |
| fulltext.url.fl_str_mv | https://bibliotecadigital.ipb.pt/bitstreams/5d06368e-9331-4475-878b-4e9c1fe722c3/download |
| id | ipb_dafa43ae19fd87a35dbff1d3aaaedfef |
| identifier.url.fl_str_mv | http://hdl.handle.net/10198/16374 |
| instacron_str | ipb |
| institution | Instituto Politécnico de Bragança |
| instname_str | Instituto Politécnico de Bragança |
| language | eng |
| network_acronym_str | ipb |
| network_name_str | Biblioteca Digital do IPB |
| oai_identifier_str | oai:bibliotecadigital.ipb.pt:10198/16374 |
| organization_str_mv | urn:organizationAcronym:ipb |
| person_str_mv | Ribeiro, António E. Ribeiro, António E. https://www.ciencia-id.pt/3211-D5B0-870D 3211-D5B0-870D http://orcid.org/0000-0003-4569-7887 0000-0003-4569-7887 Arafah, Rami Arafah, Rami https://www.ciencia-id.pt/AB16-ECBF-B886 AB16-ECBF-B886 http://orcid.org/0000-0002-7743-4988 0000-0002-7743-4988 Rodrigues, Alírio Pais, Luís S. Pais, Luís S. https://www.ciencia-id.pt/421E-0CCD-A84F 421E-0CCD-A84F http://orcid.org/0000-0002-3000-2862 0000-0002-3000-2862 |
| publishDate | 2016 |
| publisher.none.fl_str_mv | FCUL |
| reponame_str | Biblioteca Digital do IPB |
| repository_id_str | urn:repositoryAcronym:ipb |
| service_str_mv | urn:repositoryAcronym:ipb |
| spelling | engFCULpt_PTContinuous preparative liquid chromatography is nowadays a well-established technology used for the separation of a wide range of chemical mixtures. Among theseContinuous preparative liquid chromatography is nowadays a well-established technology used for the separation of a wide range of chemical mixtures. Among these techniques, the simulated moving bed (SMB) technology has gained an increasing interest to the industry in the production of fine chemicals and pharmaceuticals. This growing is due to the development of new and more versatile stationary phases, as well as new operating schemes for SMB and other continuous chromatographic processes. In recent years, the authors have focused in the preparative separation of chemical drugs by chiral SMB chromatography. Different case studies have been considered, including the separation of non-steroidal anti-inflammatory drugs (ketoprofen and flurbiprofen enantiomers) [1-4], and the pseudo-binary separation of nadolol stereoisomers, a beta-blocker pharmaceutical drug [5]. While the first two case studies are typical examples of binary chiral mixtures (a pair of enantiomers), the last is an example of a quaternary mixture, composed by two pairs of enantiomers. This considerably increases the complexity and the difficulty of the separation process, asking for new strategies for the complete resolution of all the four components. Experimental and simulation results have been recently presented considering a first step of a pseudo-binary separation by SMB (the more retained component being obtained pure in the extract and the other three co-eluting in the raffinate), followed by a ternary separation through a JO process [6]. This work introduces a different strategy using an achiral C18 stationary phase under reversed-phase mode to perform a first SMB separation step. The C18 achiral adsorbent allows the separation of the two pairs of nadolol diastereomers, i.e., the first racemate (composed by the nadolol compounds 2 and 3) co-eluting in the raffinate, and the second racemate (composed by the nadolol compounds 1 and 4) to be obtained in the extract SMB stream. After this preliminary achiral separation step, two parallel SMB runs must be carried out using a chiral stationary phase to achieve the complete separation of all the four nadolol stereoisomers.application/pdfpt_PTSeparation of Nadolol Stereoisomers by Fixed-Bed and Continuous Preparative Liquid Chromatography using C18 ColumnsPersonalRibeiro, António E.DSpacehttp://dspace.org/items/52666376-f100-4407-87ef-dc5df3613761DSpacehttp://dspace.org/items/52666376-f100-4407-87ef-dc5df3613761RibeiroAntónio E.Ciência IDhttps://www.ciencia-id.pt3211-D5B0-870DORCIDhttp://orcid.org0000-0003-4569-7887Scopus Author IDhttps://www.scopus.com23390701300Scopus Author IDhttps://www.scopus.com57202082018PersonalArafah, RamiDSpacehttp://dspace.org/items/3cd4864a-8aa6-46a2-9415-767a7551ee62DSpacehttp://dspace.org/items/3cd4864a-8aa6-46a2-9415-767a7551ee62ArafahRamiCiência IDhttps://www.ciencia-id.ptAB16-ECBF-B886ORCIDhttp://orcid.org0000-0002-7743-4988Scopus Author IDhttps://www.scopus.com57151342900Rodrigues, AlírioPersonalPais, Luís S.DSpacehttp://dspace.org/items/c6d25534-8487-45b1-90af-d350f4e3ac55DSpacehttp://dspace.org/items/c6d25534-8487-45b1-90af-d350f4e3ac55PaisLuís S.Ciência IDhttps://www.ciencia-id.pt421E-0CCD-A84FORCIDhttp://orcid.org0000-0002-3000-2862Scopus Author IDhttps://www.scopus.com6603930478HostingInstitutionOrganizationalBiblioteca Digital do IPBe-mailmailto:dspace@ipb.ptdspace@ipb.pt2018-03-19T14:57:40Z20162016-01-01T00:00:00ZHandlehttp://hdl.handle.net/10198/16374http://purl.org/coar/access_right/c_abf2open accessContinuous preparative liquid chromatographySimulated moving bed922057 bytesother research producthttp://purl.org/coar/resource_type/c_c94fconference object2016http://creativecommons.org/licenses/by/4.0/http://purl.org/coar/access_right/c_abf2application/pdffulltexthttps://bibliotecadigital.ipb.pt/bitstreams/5d06368e-9331-4475-878b-4e9c1fe722c3/downloadXVI Latin-American Congress on Chromatography & 9th National Meetoing on Chromatography249250Lisbon, Portugal |
| spellingShingle | Separation of Nadolol Stereoisomers by Fixed-Bed and Continuous Preparative Liquid Chromatography using C18 Columns Ribeiro, António E. Continuous preparative liquid chromatography Simulated moving bed |
| status | SINGLETON |
| subject.fl_str_mv | Continuous preparative liquid chromatography Simulated moving bed |
| title | Separation of Nadolol Stereoisomers by Fixed-Bed and Continuous Preparative Liquid Chromatography using C18 Columns |
| title_full | Separation of Nadolol Stereoisomers by Fixed-Bed and Continuous Preparative Liquid Chromatography using C18 Columns |
| title_fullStr | Separation of Nadolol Stereoisomers by Fixed-Bed and Continuous Preparative Liquid Chromatography using C18 Columns |
| title_full_unstemmed | Separation of Nadolol Stereoisomers by Fixed-Bed and Continuous Preparative Liquid Chromatography using C18 Columns |
| title_short | Separation of Nadolol Stereoisomers by Fixed-Bed and Continuous Preparative Liquid Chromatography using C18 Columns |
| title_sort | Separation of Nadolol Stereoisomers by Fixed-Bed and Continuous Preparative Liquid Chromatography using C18 Columns |
| topic | Continuous preparative liquid chromatography Simulated moving bed |
| topic_facet | Continuous preparative liquid chromatography Simulated moving bed |
| url | http://hdl.handle.net/10198/16374 |
| visible | 1 |