Next Article in Journal
Natural Alkaloids and Heterocycles as G-Quadruplex Ligands and Potential Anticancer Agents
Next Article in Special Issue
Chiral Thioxanthones as Modulators of P-glycoprotein: Synthesis and Enantioselectivity Studies
Previous Article in Journal
Triterpenoid Saponins from Anemone rivularis var. Flore-Minore and Their Anti-Proliferative Activity on HSC-T6 Cells
Previous Article in Special Issue
Marine Natural Peptides: Determination of Absolute Configuration Using Liquid Chromatography Methods and Evaluation of Bioactivities
Article Menu
Issue 2 (February) cover image

Export Article

Open AccessFeature PaperReview
Molecules 2018, 23(2), 492; https://doi.org/10.3390/molecules23020492

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

1
Department of Chemistry, Federal University of São Carlos—UFSCar, Rod. Washington Luis s/n, km 235, São Carlos, SP 13565-905, Brazil
2
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)
Full-Text   |   PDF [3775 KB, uploaded 24 February 2018]   |  

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. View Full-Text
Keywords: polysaccharide-based CSP; chiral chromatography; enantiomeric excess; VCD polysaccharide-based CSP; chiral chromatography; enantiomeric excess; VCD
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).
SciFeed

Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top