ReviewMolecules (Basel, Switzerland)2018
Enantiomeric Mixtures in Natural Product Chemistry: Separation and Absolute Configuration Assignment.
Review in Molecules (Basel, Switzerland), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Chiral Coumarin Enantiomers From Prangos pabularia Roots: Absolute Configuration, Tyrosinase Activation, and Anti-Vitiligo Potential in B16F10 Cells.Chemistry & biodiversity · 2026Article
- The Metabolome of theJournal of natural products · 2026Review
- Spectroscopy and Conformer-Selective Photoelectron Circular Dichroism of Chiral Molecules.Chemistry, an Asian journal · 2026Review
- Seasonal Influence on Volatile Organic Compounds from Flowers and Leaves ofPlants (Basel, Switzerland) · 2025Article
- Determination of the Absolute Configuration of Secondary Alcohols in a Compound Mixture via the Application of Competing Enantioselective Acylation Coupled with LC/MS Analysis.Pharmaceutics · 2024Article
- Role of Stereochemistry on the Biological Activity of Nature-Inspired 3-Br-Acivicin Isomers and Derivatives.Molecules (Basel, Switzerland) · 2023Article
- Absolute Stereochemistry Determination of Bioactive Marine-Derived Cyclopeptides by Liquid Chromatography Methods: An Update Review (2018-2022).Molecules (Basel, Switzerland) · 2023Review
- Natural Enantiomers: Occurrence, Biogenesis and Biological Properties.Molecules (Basel, Switzerland) · 2022Review
- Demystifying racemic natural products in the homochiral world.Nature reviews. Chemistry · 2022Review
- Sesquiterpene Lactones fromMolecules (Basel, Switzerland) · 2020Article
- Chiral Stationary Phases for Liquid Chromatography: Recent Developments.Molecules (Basel, Switzerland) · 2019Review
- Structural Elucidation and Cytotoxicity of a New 17-Membered Ring Lactone from AlgerianMolecules (Basel, Switzerland) · 2018Article
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Chiral natural product molecules are generally assumed to be biosynthesized in an enantiomerically pure or enriched fashion. Nevertheless, a significant amount of racemates or enantiomerically enriched mixtures has been reported from natural sources. This number is estimated to be even larger since the enantiomeric purity of secondary metabolites is rarely checked in the natural product isolation pipeline. This latter fact may have drastic effects on the evaluation of the biological activity of chiral natural products. A second bottleneck is the determination of their absolute configurations. Despite the widespread use of optical rotation and electronic circular dichroism, most of the stereochemical assignments are based on empirical correlations with similar compounds reported in the literature. As an alternative, the combination of vibrational circular dichroism and quantum chemical calculations has emerged as a powerful and reliable tool for both conformational and configurational analysis of natural products, even for those lacking UV-Vis chromophores. In this review, we aim to provide the reader with a critical overview of the occurrence of enantiomeric mixtures of secondary metabolites in nature as well the best practices for their detection, enantioselective separation using liquid chromatography, and determination of absolute configuration by means of vibrational circular dichroism and density functional theory calculations.
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