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Nat Prod Rep. 2019 Jul 1;36(7):1005-1030. doi: 10.1039/c9np00018f. Epub 2019 Jun 5.

Computational prediction of chiroptical properties in structure elucidation of natural products.

Author information

1
Department of Agricultural Sciences, University of Naples Federico II, Via Università 100, 80055 Portici (NA), Italy.
2
Department of Pharmacy, University of Naples Federico II, Via Domenico Montesano 49, 80131 Napoli, Italy. alfonso.mangoni@unina.it.

Abstract

Covering: up to 2019This 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.

PMID:
31166350
DOI:
10.1039/c9np00018f

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