Scalemic natural products

Rositano, Vincenzo; Senaldi, Luca; Bernardi, Anna; Allegrini, Pietro; Appendino, Giovanni

doi:10.1039/d3np00014a

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2024

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Cited by 5 publications

(1 citation statement)

References 142 publications

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“…Surprisingly, compound 12 was isolated as an unexpected scalemic mixture. This may be due to the enzymatic induction of an enantiomeric excess during biosynthesis …”

Section: Resultsmentioning

confidence: 99%

Xanthone Inhibitors of Unfolded Protein Response Isolated from Calophyllum caledonicum

Chambaud,

Le Ray,

Hamzi

et al. 2024

J. Nat. Prod.

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“…Surprisingly, compound 12 was isolated as an unexpected scalemic mixture. This may be due to the enzymatic induction of an enantiomeric excess during biosynthesis …”

Section: Resultsmentioning

confidence: 99%

Xanthone Inhibitors of Unfolded Protein Response Isolated from Calophyllum caledonicum

Chambaud,

Le Ray,

Hamzi

et al. 2024

J. Nat. Prod.

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Resolution and Absolute Configuration of Fargesin Enantiomers

Mestriner,

Lee,

Cunha

et al. 2024

Chirality

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Fargesin is an important bioactive furofuran lignan isolated from different plant species. Despite presenting potent biological activities, its stereochemical characterization has relied mostly on empirical correlations of optical rotation, an approach considered risky that commonly leads to misassignments and error propagation. Additionally, the enantiomeric purity of fargesin isolates used for biological assays has not been previously investigated. Herein, we report the enantioresolution of a scalemic mixture of fargesin isolated from Aristolochia warmingii along with the first unambiguous determination of the absolute configuration of each enantiomer by means of optical rotatory dispersion, as well as electronic and vibrational circular dichroism aided by quantum‐chemical calculations.

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Altering the mobile phase composition to enhance self-disproportionation of enantiomers in achiral chromatography

Mruc,

Olbrycht,

Korbetskyy

et al. 2024

Journal of Chromatography A

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Scalemic natural products

Abstract: In natural products, a low optical purity is not generally associated with a sloppy enzymatic activity, but rather with the co-expression of antipodal enzymes/directing proteins or, alternatively, with erosion by enzymatic or spontaneous reactions.

Cited by 5 publications

References 142 publications

Xanthone Inhibitors of Unfolded Protein Response Isolated from Calophyllum caledonicum

Xanthone Inhibitors of Unfolded Protein Response Isolated from Calophyllum caledonicum

Resolution and Absolute Configuration of Fargesin Enantiomers

Altering the mobile phase composition to enhance self-disproportionation of enantiomers in achiral chromatography

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