Issue 22, 2023

Combining the power of DP4+ and ANN-PRA analysis on stereochemical assignments: structural validation of bioactive cyclic peroxide from the marine sponge Plakortis angulospiculatus

Abstract

Nuclear magnetic resonance (NMR) spectroscopy can provide detailed information about the chemical structure and stereochemistry of a molecule. However, this technique alone may not always be sufficient to assign with confidence the relative configuration of a secondary metabolite. In some cases, additional experiments, such as the Density Functional Theory (DFT) calculation of the chemical shifts for the molecule, may be necessary to support the assignment. An endoperoxide (1) isolated from Plakortis angulospiculatus has a structure containing four stereogenic centers. The stereochemistry of 1 was proposed based on the biogenetic pathway and optical rotation correlations. Herein, we describe the structure analysis of the natural 1 by quantum NMR calculations for the first time.

Graphical abstract: Combining the power of DP4+ and ANN-PRA analysis on stereochemical assignments: structural validation of bioactive cyclic peroxide from the marine sponge Plakortis angulospiculatus

Supplementary files

Article information

Article type
Paper
Submitted
17 Apr 2023
Accepted
16 May 2023
First published
16 May 2023

New J. Chem., 2023,47, 10834-10841

Combining the power of DP4+ and ANN-PRA analysis on stereochemical assignments: structural validation of bioactive cyclic peroxide from the marine sponge Plakortis angulospiculatus

A. N. L. Batista, L. H. Martorano, A. L. Valverde and F. M. dos Santos, New J. Chem., 2023, 47, 10834 DOI: 10.1039/D3NJ01762A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements