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Stereochemical revision of xylogranatin F by GIAO and DU8+ NMR calculations.

ABSTRACT: This manuscript describes predicted NMR shifts for the limonoid natural product xylogranatin F. The ¹ H and ¹³ C NMR shifts of four diastereomers were evaluated by GIAO and hybrid DFT/parametric DU8+ methods. The results of the ¹ H and ¹³ C NMR calculations for both the GIAO method and the DU8+ calculations suggest the revised structure that was recently reassigned by chemical synthesis. Furthermore, we show that while DU8+ provides superior accuracy with less computation time, GIAO points to the correct structure with more distinguishable data in this case study.

SUBMITTER: Liu Y

PROVIDER: S-EPMC8048713 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Stereochemical revision of xylogranatin F by GIAO and DU8+ NMR calculations.

Liu Yannan Y Holt Tina A TA Kutateladze Andrei A Newhouse Timothy R TR

Chirality 20200303 5

This manuscript describes predicted NMR shifts for the limonoid natural product xylogranatin F. The 1 H and 13 C NMR shifts of four diastereomers were evaluated by GIAO and hybrid DFT/parametric DU8+ methods. The results of the 1 H and 13 C NMR calculations for both the GIAO method and the DU8+ calculations suggest the revised structure that was recently reassigned by chemical synthesis. Furthermore, we show that while DU8+ provides superior accuracy w ...[more]

PMID: 32125044

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