Revision of the Absolute Configurations of Chelocardin and Amidochelocardin

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Autoren

  • Asfandyar Sikandar
  • Alexander Popoff
  • Ravindra P. Jumde
  • Attila Mándi
  • Amninder Kaur
  • Walid A.M. Elgaher
  • Lara Rosenberger
  • Stephan Hüttel
  • Rolf Jansen
  • Maja Hunter
  • Jesko Köhnke
  • Anna K.H. Hirsch
  • Tibor Kurtán
  • Rolf Müller

Externe Organisationen

  • Helmholtz-Zentrum für Infektionsforschung GmbH (HZI)
  • University of Debrecen
  • Universität des Saarlandes
  • Merz Pharma GmbH & Co. KGaA
  • University of Glasgow
  • Helmholtz-Institut für Pharmazeutische Forschung Saarland (HIPS)
Forschungs-netzwerk anzeigen

Details

OriginalspracheEnglisch
Aufsatznummere202306437
FachzeitschriftAngewandte Chemie - International Edition
Jahrgang62
Ausgabenummer40
Frühes Online-Datum19 Juli 2023
PublikationsstatusVeröffentlicht - 25 Sept. 2023
Extern publiziertJa

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.

ASJC Scopus Sachgebiete

Zitieren

Revision of the Absolute Configurations of Chelocardin and Amidochelocardin. / Sikandar, Asfandyar; Popoff, Alexander; Jumde, Ravindra P. et al.
in: Angewandte Chemie - International Edition, Jahrgang 62, Nr. 40, e202306437, 25.09.2023.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Sikandar, A, Popoff, A, Jumde, RP, Mándi, A, Kaur, A, Elgaher, WAM, Rosenberger, L, Hüttel, S, Jansen, R, Hunter, M, Köhnke, J, Hirsch, AKH, Kurtán, T & Müller, R 2023, 'Revision of the Absolute Configurations of Chelocardin and Amidochelocardin', Angewandte Chemie - International Edition, Jg. 62, Nr. 40, e202306437. https://doi.org/10.1002/anie.202306437
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., & Müller, R. (2023). Revision of the Absolute Configurations of Chelocardin and Amidochelocardin. Angewandte Chemie - International Edition, 62(40), Artikel e202306437. https://doi.org/10.1002/anie.202306437
Sikandar A, Popoff A, Jumde RP, Mándi A, Kaur A, Elgaher WAM et al. Revision of the Absolute Configurations of Chelocardin and Amidochelocardin. Angewandte Chemie - International Edition. 2023 Sep 25;62(40):e202306437. Epub 2023 Jul 19. doi: 10.1002/anie.202306437
Sikandar, Asfandyar ; Popoff, Alexander ; Jumde, Ravindra P. et al. / Revision of the Absolute Configurations of Chelocardin and Amidochelocardin. in: Angewandte Chemie - International Edition. 2023 ; Jahrgang 62, Nr. 40.
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title = "Revision of the Absolute Configurations of Chelocardin and Amidochelocardin",
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",
author = "Asfandyar Sikandar and Alexander Popoff and Jumde, {Ravindra P.} and Attila M{\'a}ndi and Amninder Kaur and Elgaher, {Walid A.M.} and Lara Rosenberger and Stephan H{\"u}ttel and Rolf Jansen and Maja Hunter and Jesko K{\"o}hnke and Hirsch, {Anna K.H.} and Tibor Kurt{\'a}n and Rolf M{\"u}ller",
note = "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 Sk{\l}odowska-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 (KIF{\"U}) 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 Sk{\l}odowska‐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 (KIF{\"U}) 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: {\textcopyright} 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.",
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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

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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

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