Between Two Chairs: Combination of Theory and Experiment for the Determination of the Conformational Dynamics of Xylosides

Jaeschke, Sven Ole; Auer, Alexander A.

doi:10.1002/chem.202201544

Cited by 4 publications

(1 citation statement)

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“…They demonstrated that identifying the most stable conformers using the computational calculations of relative free energies or NMR chemical shifts was not sensitive, whereas the calculation of JH,H values enabled the quantification of the ratio of different conformers in the mixture. 46 The procedure of conformational analysis presented here was similar to that of Auer et al…”

Section: Discussionmentioning

confidence: 99%

Conformationally Flexible Ellagitannins: Conformational Analysis of Davidiin and Punicafolin via DFT Calculation of 1H NMR Coupling Constants

Matsuo

Iki

Okubo

et al. 2023

Preprint

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Many ellagitannins with various conformations of their glucose moiety have been isolated from natural sources. Here, a conformational analysis was performed via the density functional theory calculation of 1H NMR coupling constants. It was observed that, in the solution state, davidiin exists as an equilibrium mixture of the BO,3 (boat) and 1C4 (chair) conformational states, while punicafolin is an equilibrium mixture of the 3S1 (skew-boat) and 1C4 conformational states. Their equilibrium states changed depending on the solvent and temperature. Such conformational flexibility may be important for the biosynthesis of ellagitannins with diverse structures.

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