Revision of the Absolute Configurations of Chelocardin and Amidochelocardin

Author:

Sikandar Asfandyar1ORCID,Popoff Alexander1,Jumde Ravindra P.1,Mándi Attila2,Kaur Amninder1ORCID,Elgaher Walid A. M.1,Rosenberger Lara134,Hüttel Stephan56,Jansen Rolf56,Hunter Maja1,Köhnke Jesko17,Hirsch Anna K. H.138,Kurtán Tibor2,Müller Rolf138ORCID

Affiliation:

1. Helmholtz Institute for Pharmaceutical Research Saarland (HIPS) - Helmholtz Centre for Infection Research (HZI) Campus Building E8.1 66123 Saarbrücken Germany

2. Department of Organic Chemistry University of Debrecen P. O. Box 400 4002 Debrecen Hungary

3. Department of Pharmacy Saarland University Campus Building E8.1 66123 Saarbrücken Germany

4. Discovery and Development Technologies (DDTech) Merck KGaA Frankfurter Strasse 250 64293 Darmstadt Germany

5. German Centre for Infection Research (DZIF) Partner Site Hannover-Braunschweig 38124 Braunschweig Germany

6. Department of Microbial Drugs Helmholtz Centre for Infection Research (HZI) 38124 Braunschweig Germany

7. School of Chemistry University of Glasgow University Avenue Glasgow G12 8QQ UK

8. Helmholtz International Lab for Anti-infectives Campus Building E8.1 66123 Saarbrücken Germany

Abstract

AbstractEven 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.

Funder

Nemzeti Kutatási Fejlesztési és Innovációs Hivatal

H2020 Marie Skłodowska-Curie Actions

Deutsches Zentrum für Infektionsforschung

Publisher

Wiley

Subject

General Chemistry,Catalysis

Cited by 1 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. Study for C4-O-Glycosylation of Tetracycline;Tetrahedron Letters;2023-12

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