Issue 76, 2024

Stereochemistry of natural products from vibrational circular dichroism

Abstract

Secondary metabolites from land and marine (micro)organisms have been at the focus of the drug discovery process for many years. One of the reasons for this success is nature's incredible ability to create intricate molecular scaffolds. Such structural richness, however, makes the structural elucidation, and the absolute configuration assignment in particular, a challenging process. Vibrational circular dichroism (VCD) has emerged as one of the most reliable and versatile methods to unambiguously assign both the absolute configuration and conformations of chiral molecules in solution. Although VCD is no longer a curiosity in the field of molecular spectroscopy after 50 years since its first report, it is still underutilized by natural product chemists worldwide for varying reasons. Herein, we highlight the evolution of the application of VCD to natural product chemistry, focusing on its strengths as well as points that still need improvement. General guidelines for the correct application of VCD to stereochemical studies are also provided.

Graphical abstract: Stereochemistry of natural products from vibrational circular dichroism

Supplementary files

Article information

Article type
Highlight
Submitted
22 mai 2024
Accepted
23 aug 2024
First published
26 aug 2024

Chem. Commun., 2024,60, 10439-10450

Stereochemistry of natural products from vibrational circular dichroism

A. N. L. Batista, A. L. Valverde, L. A. Nafie and J. M. Batista Jr, Chem. Commun., 2024, 60, 10439 DOI: 10.1039/D4CC02481H

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