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Resolution and Absolute Configuration Assignment of a Natural Racemic Chromane from Peperomia obtusifolia (Piperaceae)

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dc.contributor.authorBatista, Joao Marcos [UNESP]
dc.contributor.authorLopez, Silvia Noeli [UNESP]
dc.contributor.authorMota, Jonas da Silva
dc.contributor.authorVanzolini, Kenia Lourenco
dc.contributor.authorCass, Quezia Bezerra
dc.contributor.authorRinaldo, Daniel
dc.contributor.authorVilegas, Wagner [UNESP]
dc.contributor.authorBolzani, Vanderlan da Silva [UNESP]
dc.contributor.authorKato, Massuo Jorge
dc.contributor.authorFurlan, Maysa [UNESP]
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionUniversidade Estadual de Mato Grosso do Sul (UEMS)
dc.contributor.institutionUniversidade Federal de São Carlos (UFSCar)
dc.contributor.institutionUniversidade de São Paulo (USP)
dc.date.accessioned2014-05-20T14:21:15Z
dc.date.available2014-05-20T14:21:15Z
dc.date.issued2009-10-01
dc.description.abstractThe resolution of the natural racemic chromane 3,4-dihydro-5-hydroxy-2,7-dimethyl-8-(3 ''-methyl-2 ''-butenyl)-2-(4'-methyl-1',3'-pentadienyl)-2H-1-benzopyran-6-carboxylic acid (1) isolated from the leaves of Peperomia obtusifolia has been accomplished using stereoselective HPLC. The absolute coil figuration of the resolved enantiomers was determined by the analysis of optical rotations and CD spectra. The finding of a racemic mixture instead of an enantiomerically pure metabolite raises questions about the final steps in the biosynthesis of this class of natural products, suggesting that the intramolecular chromane ring formation step may not be enzymatically controlled at all in P. obtusifolia. Chirality 21:799-801, 2009. (C) 2008 Wiley-Liss, Inc.en
dc.description.affiliationSão Paulo State Univ, UNESP, Dept Organ Chem, Inst Chem,NuBBE Nucleus Bioassays Biosynthesis &, BR-14800900 Araraquara, SP, Brazil
dc.description.affiliationMato Grosso State Univ UEMS, Dourados, MS, Brazil
dc.description.affiliationUniversidade Federal de São Carlos (UFSCar), Dept Chem, BR-13560 São Carlos, SP, Brazil
dc.description.affiliationUniv São Paulo, Inst Chem, São Paulo, Brazil
dc.description.affiliationUnespSão Paulo State Univ, UNESP, Dept Organ Chem, Inst Chem,NuBBE Nucleus Bioassays Biosynthesis &, BR-14800900 Araraquara, SP, Brazil
dc.format.extent799-801
dc.identifierhttp://dx.doi.org/10.1002/chir.20676
dc.identifier.citationChirality. Hoboken: Wiley-liss, v. 21, n. 9, p. 799-801, 2009.
dc.identifier.doi10.1002/chir.20676
dc.identifier.issn0899-0042
dc.identifier.lattes4484083685251673
dc.identifier.lattes1308042794786872
dc.identifier.orcid0000-0003-3032-2556
dc.identifier.urihttp://hdl.handle.net/11449/26359
dc.identifier.wosWOS:000270008800002
dc.language.isoeng
dc.publisherWiley-liss
dc.relation.ispartofChirality
dc.relation.ispartofjcr1.833
dc.relation.ispartofsjr0,536
dc.rights.accessRightsAcesso restrito
dc.sourceWeb of Science
dc.subjectnatural productsen
dc.subjectenantioseparationen
dc.subjectcircular dichroismen
dc.subjectoptical rotationen
dc.subjectabsolute configurationen
dc.titleResolution and Absolute Configuration Assignment of a Natural Racemic Chromane from Peperomia obtusifolia (Piperaceae)en
dc.typeArtigo
dcterms.licensehttp://olabout.wiley.com/WileyCDA/Section/id-406071.html
dcterms.rightsHolderWiley-liss
dspace.entity.typePublication
unesp.author.lattes4484083685251673
unesp.author.lattes1308042794786872
unesp.author.orcid0000-0001-5363-6481[6]
unesp.author.orcid0000-0003-3032-2556[7]
unesp.campusUniversidade Estadual Paulista (UNESP), Instituto de Química, Araraquarapt
unesp.departmentQuímica Orgânica - IQARpt

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Araraquara - IQAR - Instituto de Química