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Vibrational Circular Dichroism for the Assignment of Absolute Configuration of Natural Products in Brazil

Authors :
Fernando M. dos Santos
Alessandra L. Valverde
João M. Batista
Andrea N. L. Batista
Source :
Revista Brasileira de Farmacognosia. 31:612-624
Publication Year :
2021
Publisher :
Springer Science and Business Media LLC, 2021.

Abstract

The determination of the absolute configuration of chiral bioactive natural products is a crucial step in their structural characterization. Several well-established techniques, such as X-ray crystallography, stereo-controlled organic synthesis, NMR, and chiroptical spectroscopy, are commonly used to this end. However, even today, the configurational analysis of natural products remains a challenge, with a significant number of reassignments being reported every year. Among chiroptical methods, vibrational circular dichroism (VCD) has emerged as an excellent tool for the assignment of the absolute configuration of structurally diverse chiral natural products directly in solution. This review covers the use of VCD spectroscopy to elucidate the absolute stereochemistry of natural products in Brazil over the last 20 years. Although the number of VCD investigations on secondary metabolites has increased, VCD can still be considered under-explored in Brazil. Therefore, herein, we aim to demonstrate the unparalleled stereochemical discriminatory power of VCD to assign both conformation and absolute configuration of natural products in conditions not commonly accessible to other techniques.

Details

ISSN :
1981528X
Volume :
31
Database :
OpenAIRE
Journal :
Revista Brasileira de Farmacognosia
Accession number :
edsair.doi...........7188c8a72d12554cb63e7713d5c037cc
Full Text :
https://doi.org/10.1007/s43450-021-00184-z