Issue 7, 2019

Computational prediction of chiroptical properties in structure elucidation of natural products

Abstract

Covering: up to 2019

This review covers the current status of the quantum mechanical prediction of chiroptical properties, such as electronic CD and optical rotation, as needed for stereochemical assignments in new natural products. The reliability of the prediction of chiroptical properties is steadily increasing, with a parallel decrease in the required computational resources. Now, quantum mechanical calculations for a medium-sized natural product can be reliably performed by natural product chemists on a mainstream PC. This review is aimed to guide natural product chemists through the numerous steps involved in such calculations. Through a concise, but comprehensive, discussion of the current computational practice, enriched by a few illustrative examples, this review provides readers with the theoretical background and practical knowledge needed to select the most appropriate parameters for performing the calculations, to anticipate possible problems, and to critically evaluate the reliability of their computational results. Common reasons for mistakes are also discussed; in particular, the importance of the correct evaluation of conformational ensembles of flexible molecules (an aspect often overlooked in current research) is stressed.

Graphical abstract: Computational prediction of chiroptical properties in structure elucidation of natural products

Article information

Article type
Review Article
Submitted
03 mar. 2019
First published
05 jun. 2019

Nat. Prod. Rep., 2019,36, 1005-1030

Computational prediction of chiroptical properties in structure elucidation of natural products

L. Grauso, R. Teta, G. Esposito, M. Menna and A. Mangoni, Nat. Prod. Rep., 2019, 36, 1005 DOI: 10.1039/C9NP00018F

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