A combined Raman optical activity and vibrational circular dichroism study on artemisinin-type products
- Author
- Jonathan Bogaerts, Filip Desmet, Roy Aerts, Patrick Bultinck (UGent) , Wouter Herrebout and Christian Johannessen
- Organization
- Abstract
- Artemisinin and two of its derivatives, dihydroartemisinin and artesunate, which are front line drugs against malaria, were investigated using Raman optical activity (ROA) and vibrational circular dichroism (VCD) experiments, both supported by density functional theory (DFT) level calculations. The experimental techniques combined with DFT calculations could show that dihydroartemisinin was present as an epimeric mixture in solution. In addition, an approximation of the epimeric ratio could be extracted which was in agreement with the ratio obtained by(1)H-NMR spectroscopy. The current study also demonstrates that both ROA and VCD are able to assign the correct absolute configuration (AC) of artemisinin and artesunate out of all their possible diastereomers without any explicit knowledge on their correct stereochemistry and accentuates the synergetic effect between ROA and VCD in AC determination.
- Keywords
- ABSOLUTE-CONFIGURATION, STEREOCHEMICAL CHARACTERIZATION, ACTIVITY, SPECTRA, IR
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-8689183
- MLA
- Bogaerts, Jonathan, et al. “A Combined Raman Optical Activity and Vibrational Circular Dichroism Study on Artemisinin-Type Products.” PHYSICAL CHEMISTRY CHEMICAL PHYSICS, vol. 22, no. 32, Royal Soc Chemistry, 2020, pp. 18014–24, doi:10.1039/d0cp03257c.
- APA
- Bogaerts, J., Desmet, F., Aerts, R., Bultinck, P., Herrebout, W., & Johannessen, C. (2020). A combined Raman optical activity and vibrational circular dichroism study on artemisinin-type products. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 22(32), 18014–18024. https://doi.org/10.1039/d0cp03257c
- Chicago author-date
- Bogaerts, Jonathan, Filip Desmet, Roy Aerts, Patrick Bultinck, Wouter Herrebout, and Christian Johannessen. 2020. “A Combined Raman Optical Activity and Vibrational Circular Dichroism Study on Artemisinin-Type Products.” PHYSICAL CHEMISTRY CHEMICAL PHYSICS 22 (32): 18014–24. https://doi.org/10.1039/d0cp03257c.
- Chicago author-date (all authors)
- Bogaerts, Jonathan, Filip Desmet, Roy Aerts, Patrick Bultinck, Wouter Herrebout, and Christian Johannessen. 2020. “A Combined Raman Optical Activity and Vibrational Circular Dichroism Study on Artemisinin-Type Products.” PHYSICAL CHEMISTRY CHEMICAL PHYSICS 22 (32): 18014–18024. doi:10.1039/d0cp03257c.
- Vancouver
- 1.Bogaerts J, Desmet F, Aerts R, Bultinck P, Herrebout W, Johannessen C. A combined Raman optical activity and vibrational circular dichroism study on artemisinin-type products. PHYSICAL CHEMISTRY CHEMICAL PHYSICS. 2020;22(32):18014–24.
- IEEE
- [1]J. Bogaerts, F. Desmet, R. Aerts, P. Bultinck, W. Herrebout, and C. Johannessen, “A combined Raman optical activity and vibrational circular dichroism study on artemisinin-type products,” PHYSICAL CHEMISTRY CHEMICAL PHYSICS, vol. 22, no. 32, pp. 18014–18024, 2020.
@article{8689183,
abstract = {{Artemisinin and two of its derivatives, dihydroartemisinin and artesunate, which are front line drugs against malaria, were investigated using Raman optical activity (ROA) and vibrational circular dichroism (VCD) experiments, both supported by density functional theory (DFT) level calculations. The experimental techniques combined with DFT calculations could show that dihydroartemisinin was present as an epimeric mixture in solution. In addition, an approximation of the epimeric ratio could be extracted which was in agreement with the ratio obtained by(1)H-NMR spectroscopy. The current study also demonstrates that both ROA and VCD are able to assign the correct absolute configuration (AC) of artemisinin and artesunate out of all their possible diastereomers without any explicit knowledge on their correct stereochemistry and accentuates the synergetic effect between ROA and VCD in AC determination.}},
author = {{Bogaerts, Jonathan and Desmet, Filip and Aerts, Roy and Bultinck, Patrick and Herrebout, Wouter and Johannessen, Christian}},
issn = {{1463-9076}},
journal = {{PHYSICAL CHEMISTRY CHEMICAL PHYSICS}},
keywords = {{ABSOLUTE-CONFIGURATION,STEREOCHEMICAL CHARACTERIZATION,ACTIVITY,SPECTRA,IR}},
language = {{eng}},
number = {{32}},
pages = {{18014--18024}},
publisher = {{Royal Soc Chemistry}},
title = {{A combined Raman optical activity and vibrational circular dichroism study on artemisinin-type products}},
url = {{http://doi.org/10.1039/d0cp03257c}},
volume = {{22}},
year = {{2020}},
}
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