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Enantiomeric Mixtures in Natural Product Chemistry: Separation and Absolute Configuration Assignment

N L Batista, Andrea ; M Dos Santos, Fernando ; Batista, João M ; Cass, Quezia B

Molecules (Basel, Switzerland), 2018-02, Vol.23 (2), p.492 [Periódico revisado por pares]

Switzerland: MDPI AG

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Título:
Enantiomeric Mixtures in Natural Product Chemistry: Separation and Absolute Configuration Assignment
Autor: N L Batista, Andrea ; M Dos Santos, Fernando ; Batista, João M ; Cass, Quezia B
Assuntos: Absolute configuration ; Biological activity ; Biological effects ; Biological Products - chemistry ; Biological Products - isolation & purification ; chiral chromatography ; Chromatography ; Chromophores ; Circular Dichroism ; Configurations ; Density functional theory ; Dichroism ; Empirical analysis ; enantiomeric excess ; Enantiomers ; Liquid chromatography ; Metabolites ; Models, Theoretical ; Molecular Structure ; Natural products ; Optical rotation ; Pharmaceutical Preparations - chemistry ; Pharmaceutical Preparations - isolation & purification ; polysaccharide-based CSP ; Quantum chemistry ; Review ; Secondary Metabolism ; Secondary metabolites ; Separation ; Spectrum Analysis ; VCD ; Workflow
É parte de: Molecules (Basel, Switzerland), 2018-02, Vol.23 (2), p.492
Notas: ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-3
content type line 23
ObjectType-Review-1
Descrição: 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.
Editor: Switzerland: MDPI AG
Idioma: Inglês

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Enantiomeric Mixtures in Natural Product Chemistry: Separation and Absolute Configuration Assignment

N L Batista, Andrea ; M Dos Santos, Fernando ; Batista, João M ; Cass, Quezia B

Switzerland: MDPI AG

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