A combined Raman optical activity and vibrational circular dichroism study on artemisinin-type products.,Physical Chemistry Chemical Physics

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A combined Raman optical activity and vibrational circular dichroism study on artemisinin-type products.
Physical Chemistry Chemical Physics ( IF 2.9 ) Pub Date : 2020-07-29 , DOI: 10.1039/d0cp03257c
Jonathan Bogaerts ₁ , Filip Desmet ₁ , Roy Aerts ₁ , Patrick Bultinck ₂ , Wouter Herrebout ₁ , Christian Johannessen ₁

Affiliation

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 ¹H-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.

中文翻译：

青蒿素类产品的拉曼光学活性和振动圆二色性的组合研究。

使用拉曼光学活性（ROA）和振动圆二色性（VCD）实验研究了青蒿素及其两个衍生物二氢青蒿素和青蒿琥酯（它们是抗疟疾的一线药物），这两个实验均受密度泛函理论（DFT）水平计算的支持。与DFT计算相结合的实验技术可以表明，双氢青蒿素以溶液中的差向异构体混合物形式存在。此外，差向异构体比例的近似值可以提取这与由获得的比率协议¹1 H-NMR光谱。当前的研究还表明，ROA和VCD都能够从所有可能的非对映异构体中分配青蒿素和青蒿琥酯的正确绝对构型（AC），而无需对它们的正确立体化学有任何明确的了解，并增强了ROA和VCD在AC中的协同作用决心。

更新日期：2020-08-25

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