Variable-temperature NMR and conformational analysis of oenothein B
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Data
2014-02
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Resumo
Oenothein B is a dimeric hydrolysable tannin with a wide range of biological activities, such
as antitumour, anti-inflammatory and antiviral. Its nuclear magnetic resonance (NMR) at room
temperature show duplications and broadening of signals. Experiments of 1D and 2D NMR at lower
temperatures were useful for the complete NMR assignments of all hydrogens and carbons. The 3D
structure of the most stable conformer was determined for the first time by nuclear Overhauser effect
spectroscopy (NOESY) experiment (–20 ºC) and density functional theory (DFT)(B3LYP/6-31G)/
polarizable continuum model (PCM) quantum chemical calculations. The favoured conformation
showed a highly compacted geometry and a lack of symmetry, in which the two valoneoyl groups
showed distinct conformational parameters and stabilities.
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Oenothein B, Variable-temperature NMR, Macrocyclic dimer, Conformational analysis
Citação
SANTOS, Suzana C. et al. Variable-temperature NMR and conformational analysis of oenothein B. Journal of the Brazilian Chemical Society, São Paulo, v. 25, n. 2, p. 282-289, Feb. 2014.