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Enantioseparation and chiral recognition mechanism of new chiral derivatives of xanthones on macrocyclic antibiotic stationary phases

2012Journal article Open access
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dc.contributor.authorFernandes, Carla
dc.contributor.authorTiritan, Maria Elizabeth
dc.contributor.authorCass, Quezia
dc.contributor.authorKairys, Visvaldas
dc.contributor.authorFernandes, Miguel Xavier
dc.contributor.authorPinto, Madalena
dc.date.accessioned2023-02-09T12:10:12Z
dc.date.available2023-02-09T12:10:12Z
dc.date.issued2012
dc.description.abstractA chiral HPLC method using four macrocyclic antibiotic chiral stationary phases (CSPs) has been inves tigated for determination of the enantiomeric purity of fourteen new chiral derivatives of xanthones (CDXs). The separations were performed with the CSPs Chirobiotic T, Chirobiotic TAG, Chirobiotic V and Chirobiotic R under multimodal elution conditions (normal-phase, reversed-phase and polar ionic mode). The analyses were performed at room temperature in isocratic mode and UV and CD detection at a wavelength of 254 nm. The best enantioselectivity and resolution were achieved on Chirobiotic R and Chirobiotic T CSPs, under normal elution conditions, with RS ranging from 1.25 to 2.50 and from 0.78 to 2.06, respectively. The optimized chromatographic conditions allowed the determination of the enan tiomeric ratio of eight CDXs, always higher than 99%. In order to better understand the chromatographic behavior at a molecular level, and the structural features associated with the chiral recognition mech anism, computational studies by molecular docking were carried out using VDock. These studies shed light on the mechanisms involved in the enantioseparation for this important class of chiral compounds.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationFernandes, C., Tiritan, M. E., Cass, Q., Kairys, V., Fernandes, M. X., & Pinto, M. (2012). Enantioseparation and chiral recognition mechanism of new chiral derivatives of xanthones on macrocyclic antibiotic stationary phases. Journal of Chromatography A, 1241, 60-68.pt_PT
dc.identifier.doi10.1016/j.chroma.2012.04.011pt_PT
dc.identifier.urihttp://hdl.handle.net/10400.13/5021
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherElsevierpt_PT
dc.relationStrategic Project - UI 4040 - 2011-2012
dc.relationStrategic Project - UI 674 - 2011-2012
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subjectMacrocyclic antibioticpt_PT
dc.subjectChiral stationary phasespt_PT
dc.subjectChiral derivatives of xanthonespt_PT
dc.subjectEnantioselectivitypt_PT
dc.subjectEnantiomeric puritypt_PT
dc.subjectChiral recognitionpt_PT
dc.subject.pt_PT
dc.subjectFaculdade de Ciências Exatas e da Engenhariapt_PT
dc.titleEnantioseparation and chiral recognition mechanism of new chiral derivatives of xanthones on macrocyclic antibiotic stationary phasespt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleStrategic Project - UI 4040 - 2011-2012
oaire.awardTitleStrategic Project - UI 674 - 2011-2012
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/PEst-OE%2FSAU%2FUI4040%2F2011/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/PEst-OE%2FQUI%2FUI0674%2F2011/PT
oaire.citation.endPage68pt_PT
oaire.citation.startPage60pt_PT
oaire.citation.titleJournal of Chromatography Apt_PT
oaire.citation.volume1241pt_PT
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
person.familyNameKairys
person.familyNameFernandes
person.givenNameVisvaldas
person.givenNameMiguel Xavier
person.identifierK-9893-2013
person.identifier.ciencia-idA716-F916-AFB2
person.identifier.ciencia-idED1D-3C7A-467C
person.identifier.orcid0000-0002-5427-0175
person.identifier.orcid0000-0002-1840-616X
person.identifier.ridA-4373-2013
person.identifier.scopus-author-id6602925161
person.identifier.scopus-author-id35466972500
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
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