Solution-state conformations of natural products from chiroptical spectroscopy: the case of isocorilagin

Registro completo de metadados
MetadadosDescriçãoIdioma
Autor(es): dc.creatorSprenger, R. F.-
Autor(es): dc.creatorThomasi, S. S.-
Autor(es): dc.creatorFerreira, A. G.-
Autor(es): dc.creatorCass, Q. B.-
Autor(es): dc.creatorBatista Junior, J. M.-
Data de aceite: dc.date.accessioned2026-02-09T11:47:41Z-
Data de disponibilização: dc.date.available2026-02-09T11:47:41Z-
Data de envio: dc.date.issued2019-01-25-
Data de envio: dc.date.issued2019-01-25-
Data de envio: dc.date.issued2016-
Fonte completa do material: dc.identifierhttps://repositorio.ufla.br/handle/1/32515-
Fonte completa do material: dc.identifierhttps://pubs.rsc.org/en/Content/ArticleLanding/2016/OB/C6OB00049E#!divAbstract-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/capes/1147611-
Descrição: dc.descriptionIsocorilagin, the α-anomer of the ellagitannin corilagin, has been frequently reported in the literature as a constituent of various plant species. Its identification is based mainly on the smaller value for the coupling constant of its anomeric proton when compared to that of corilagin. A careful investigation of the corilagin structure in both methanol and DMSO solutions using NMR, electronic and vibrational CD, and DFT and MD calculations confirmed that isocorilagin is the result of a solvent-induced conformational transition of corilagin, rather than its diastereoisomer. Corilagin changes from B1,4 and oS5 conformations of the β-glucose core in DMSO-d6 to an inverted 1C4 conformation in methanol-d4, which accounts for NMR observables attributed to the alleged α-anomer. This misassignment reinforces the risks of relying upon a single technique for structural elucidation and stereochemical analysis of complex natural products, especially those containing saccharide moieties.-
Idioma: dc.languageen-
Publicador: dc.publisherRoyal Societyof Chemistry-
Direitos: dc.rightsrestrictAccess-
???dc.source???: dc.sourceOrganic & Biomolecular Chemistry-
Palavras-chave: dc.subjectChiroptical spectroscopy-
Palavras-chave: dc.subjectIsocorilagin-
Palavras-chave: dc.subjectEspectroscopia de quiropraxia-
Palavras-chave: dc.subjectIsocorilagina-
Título: dc.titleSolution-state conformations of natural products from chiroptical spectroscopy: the case of isocorilagin-
Tipo de arquivo: dc.typeArtigo-
Aparece nas coleções:Repositório Institucional da Universidade Federal de Lavras (RIUFLA)

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