Details
| Original language | English |
|---|---|
| Article number | e202306437 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 62 |
| Issue number | 40 |
| Early online date | 19 Jul 2023 |
| Publication status | Published - 25 Sept 2023 |
| Externally published | Yes |
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.
Keywords
- Amidochelocardin, Chelocardin, Circular Dichroism, Crystallography, Stereochemistry
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- General Chemistry
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In: Angewandte Chemie - International Edition, Vol. 62, No. 40, e202306437, 25.09.2023.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Revision of the Absolute Configurations of Chelocardin and Amidochelocardin
AU - Sikandar, Asfandyar
AU - Popoff, Alexander
AU - Jumde, Ravindra P.
AU - Mándi, Attila
AU - Kaur, Amninder
AU - Elgaher, Walid A.M.
AU - Rosenberger, Lara
AU - Hüttel, Stephan
AU - Jansen, Rolf
AU - Hunter, Maja
AU - Köhnke, Jesko
AU - Hirsch, Anna K.H.
AU - Kurtán, Tibor
AU - Müller, Rolf
N1 - Funding 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). The Governmental Information-Technology Development Agency (KIFÜ) is acknowledged for CPU time. We would like to acknowledge use of Swiss Light Source beamline X10SA and thank the beamline staff. Open Access funding enabled and organized by Projekt DEAL. Funding 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). The Governmental Information‐Technology Development Agency (KIFÜ) is acknowledged for CPU time. We would like to acknowledge use of Swiss Light Source beamline X10SA and thank the beamline staff. Open Access funding enabled and organized by Projekt DEAL. Publisher Copyright: © 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
PY - 2023/9/25
Y1 - 2023/9/25
N2 - 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.
AB - 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.
KW - Amidochelocardin
KW - Chelocardin
KW - Circular Dichroism
KW - Crystallography
KW - Stereochemistry
UR - http://www.scopus.com/inward/record.url?scp=85168278302&partnerID=8YFLogxK
U2 - 10.1002/anie.202306437
DO - 10.1002/anie.202306437
M3 - Article
C2 - 37466921
AN - SCOPUS:85168278302
VL - 62
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 40
M1 - e202306437
ER -