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Albendazole sulfoxide enantiomers: Preparative chiral separation and absolute stereochemistry

dc.contributor.authorLourenco, Tiago C.
dc.contributor.authorBatista, Joao M. [UNESP]
dc.contributor.authorFurlan, Maysa [UNESP]
dc.contributor.authorHe, Yanan
dc.contributor.authorNafie, Laurence A.
dc.contributor.authorSantana, Cesar C.
dc.contributor.authorCass, Quezia B.
dc.contributor.institutionUniversidade Federal de São Carlos (UFSCar)
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionBioTools Inc
dc.contributor.institutionSyracuse Univ
dc.contributor.institutionUniversidade Estadual de Campinas (UNICAMP)
dc.date.accessioned2014-05-20T14:21:12Z
dc.date.available2014-05-20T14:21:12Z
dc.date.issued2012-03-23
dc.description.abstractThe enantiomeric separation of albendazole sulfoxide was carried out by simulated moving bed chromatography with variable zones (VARICOL). An overall recovery of 97% was achieved and enantiomeric ratios of 99.5% for raffinate and 99.0% for extract were attained. A total of 880 mg of (+)-albendazol sulfoxide and 930 mg of its antipode were collected after 55 cycles or 11 h of process, resulting in a mass rate of 2 g/day. Furthermore the absolute configuration of the enantiopure compounds was determined for the first time by vibrational circular dichroism (VCD) with the aid of theoretical calculations as (-)-(S) and (+)-(R)-albendazole sulfoxide. (C) 2012 Elsevier B.V. All rights reserved.en
dc.description.affiliationUniversidade Federal de São Carlos (UFSCar), Dept Chem, BR-13565905 São Carlos, SP, Brazil
dc.description.affiliationSão Paulo State Univ UNESP, Dept Organ Chem, BR-14800900 Araraquara, SP, Brazil
dc.description.affiliationBioTools Inc, Jupiter, FL 33458 USA
dc.description.affiliationSyracuse Univ, Dept Chem, Syracuse, NY 13244 USA
dc.description.affiliationState Univ Campinas UNICAMP, Sch Chem Engn, Dept Biotechnol Proc, BR-13083970 Campinas, SP, Brazil
dc.description.affiliationUnespSão Paulo State Univ UNESP, Dept Organ Chem, BR-14800900 Araraquara, SP, Brazil
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.description.sponsorshipCenter for Scientific Computing (NCC/GridUNESP) of the São Paulo State University (UNESP)
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.description.sponsorshipIdFAPESP: 09/18515-1
dc.description.sponsorshipIdFAPESP: 08/58658-3
dc.description.sponsorshipIdFAPESP: 09/17138-0
dc.description.sponsorshipIdFAPESP: 07/02872-4
dc.format.extent61-65
dc.identifierhttp://dx.doi.org/10.1016/j.chroma.2012.01.070
dc.identifier.citationJournal of Chromatography A. Amsterdam: Elsevier B.V., v. 1230, p. 61-65, 2012.
dc.identifier.doi10.1016/j.chroma.2012.01.070
dc.identifier.issn0021-9673
dc.identifier.lattes1308042794786872
dc.identifier.urihttp://hdl.handle.net/11449/26344
dc.identifier.wosWOS:000301959700009
dc.language.isoeng
dc.publisherElsevier B.V.
dc.relation.ispartofJournal of Chromatography A
dc.relation.ispartofjcr3.716
dc.relation.ispartofsjr1,378
dc.rights.accessRightsAcesso restrito
dc.sourceWeb of Science
dc.subjectAlbendazole sulfoxideen
dc.subjectSimulated moving bed chromatographyen
dc.subjectVARICOL processen
dc.subjectMultimilligram enantiomeric separationen
dc.subjectVibrational circular dichroismen
dc.subjectAbsolute configurationen
dc.titleAlbendazole sulfoxide enantiomers: Preparative chiral separation and absolute stereochemistryen
dc.typeArtigo
dcterms.licensehttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
dcterms.rightsHolderElsevier B.V.
dspace.entity.typePublication
unesp.author.lattes1308042794786872
unesp.campusUniversidade Estadual Paulista (UNESP), Instituto de Química, Araraquarapt
unesp.departmentQuímica Orgânica - IQARpt

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