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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
Batista, Andrea N. L. [1] ; dos Santos, Jr., Fernando M. [1] ; Batista, Jr., Joao M. [1, 2] ; Cass, Quezia B. [1]
Total Authors: 4
Affiliation:
[1] Fed Univ Sao Carlos UFSCar, Dept Chem, Rod Washington Luis S-N, Km 235, BR-13565905 Sao Carlos, SP - Brazil
[2] Fed Univ Sao Paulo UNIFESP, Inst Sci & Technol, R Talim 330, BR-12231280 Sao Jose Dos Campos, SP - Brazil
Total Affiliations: 2
Document type: Review article
Source: Molecules; v. 23, n. 2 FEB 2018.
Web of Science Citations: 15
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. (AU)

FAPESP's process: 13/01710-1 - Enzyme ligand: new models of screening
Grantee:Quezia Bezerra Cass
Support Opportunities: Research Projects - Thematic Grants
FAPESP's process: 16/23794-0 - Stereochemistry of complex natural compounds by vibrational optical activity: acetogenins
Grantee:Fernando Martins dos Santos Junior
Support Opportunities: Scholarships in Brazil - Post-Doctoral
FAPESP's process: 14/25222-9 - Vibrational chiroptical spectroscopy for stereochemical characterization of small molecules and macromolecules
Grantee:João Marcos Batista Junior
Support Opportunities: Research Grants - Young Investigators Grants
FAPESP's process: 15/07089-2 - Vibrational chiroptical spectroscopy for stereochemical characterization of small molecules and macromolecules
Grantee:João Marcos Batista Junior
Support Opportunities: Scholarships in Brazil - Young Researchers