Use este identificador para citar ou linkar para este item: http://repositorio.ufla.br/jspui/handle/1/32515
Título: Solution-state conformations of natural products from chiroptical spectroscopy: the case of isocorilagin
Palavras-chave: Chiroptical spectroscopy
Isocorilagin
Espectroscopia de quiropraxia
Isocorilagina
Data do documento: 2016
Editor: Royal Societyof Chemistry
Citação: SPRENGER, R. F. et al. Solution-state conformations of natural products from chiroptical spectroscopy: the case of isocorilagin. Organic & Biomolecular Chemistry, Cambridge, v. 14, p. 3369-3375, 2016.
Resumo: Isocorilagin, 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.
URI: https://pubs.rsc.org/en/Content/ArticleLanding/2016/OB/C6OB00049E#!divAbstract
http://repositorio.ufla.br/jspui/handle/1/32515
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