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Revision of the absolute configurations of chelocardin and amidochelocardin

Sikandar, A. et al. (2023) Revision of the absolute configurations of chelocardin and amidochelocardin. Angewandte Chemie International Edition, 62(40), e202306437. (doi: 10.1002/anie.202306437) (PMID:37466921)

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Abstract

Even with the aid of the available methods, the configurational assignment of natural products can be a challenging task that is prone to errors, and it sometimes needs to be corrected after total synthesis or single-crystal X-ray diffraction (XRD) analysis. Herein, the absolute configuration of amidochelocardin is revised using a combination of XRD, NMR spectroscopy, experimental ECD spectra, and time-dependent density-functional theory (TDDFT)-ECD calculations. As amidochelocardin was obtained via biosynthetic engineering of chelocardin, we propose the same absolute configuration for chelocardin based on the similar biosynthetic origins of the two compounds and result of TDDFT-ECD calculations. The evaluation of spectral data of two closely related analogues, 6-desmethyl-chelocardin and its semisynthetic derivative 1, also supports this conclusion.

Item Type:Articles
Additional Information:T. K. and A. M. were supported by the National Research, Development and Innovation Office (K138672 and FK134653). The European Commission is acknowledged for an Intra-European Marie Skłodowska-Curie actions fellowship under Horizon-2020 (796089-NovInDXS, R.P.J.). The remaining authors were funded by DZIF grant (TTU09.824). OpenAccess funding enabled and organized by Projekt DEAL.
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Koehnke, Professor Jesko
Authors: Sikandar, A., Popoff, A., Jumde, R. P., Mándi, A., Kaur, A., Elgaher, W. A. M., Rosenberger, L., Hüttel, S., Jansen, R., Hunter, M., Köhnke, J., Hirsch, A. K. H., Kurtán, T., and Müller, R.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Angewandte Chemie International Edition
Publisher:Wiley
ISSN:1433-7851
ISSN (Online):1521-3773
Published Online:19 July 2023
Copyright Holders:Copyright © 2023 The Authors
First Published:First published in Angewandte Chemie International Edition 62(40):e202306437
Publisher Policy:Reproduced under a Creative Commons licence

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