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Molecules 2018, 23(2), 492;

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

Department of Chemistry, Federal University of São Carlos—UFSCar, Rod. Washington Luis s/n, km 235, São Carlos, SP 13565-905, Brazil
Institute of Science and Technology, Federal University of São Paulo—UNIFESP, R. Talim 330, São José dos Campos, SP 12231-280, Brazil
Authors to whom correspondence should be addressed.
Received: 21 December 2017 / Revised: 23 January 2018 / Accepted: 21 February 2018 / Published: 23 February 2018
(This article belongs to the Special Issue Chirality in Health and Environment: Recent developments)
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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. View Full-Text
Keywords: polysaccharide-based CSP; chiral chromatography; enantiomeric excess; VCD polysaccharide-based CSP; chiral chromatography; enantiomeric excess; VCD

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N. L. Batista, A.; M. dos Santos, F.; Batista, J.M.; Cass, Q.B. Enantiomeric Mixtures in Natural Product Chemistry: Separation and Absolute Configuration Assignment. Molecules 2018, 23, 492.

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