Research Progress: NKU Team Discovered New Method of Radical Reaction

The Method Facilitates the Configuration Flipping of Drug’s Molecule at Fixed Point

2018.08.06

The Figure shows the application of C-H Epimerization to achieve the structural transformation of pregnanediol

The research team led by Prof. Gong Chen, State Key Laboratory of Elemento-organic Chemistry, Nankai University, discovered a new method of organic chemical reaction, facilitating an efficient “configuration flipping of a tertiary carbon chiral center with non-acid protons”, which bothered the chemical society for years. As an important progress in the area of radical chemistry, the result also provides a convenient and high-efficient tool of configuration flipping for organic synthesis and drug molecule’s structural transformation. Now the related paper has been published on Journal of the American Chemical Society, the internationally well-known academic journal.

The Accurate regulation and control of stereochemistry is always a key issue in organic chemical synthesis. “Generally speaking, it means that researchers can actively and accurately control the 3D stereochemical structure of complexed molecules. The structure of the molecule directly affects its functions, for example, the transformation of drug’s chemical structure could change its functions. Thus, whether ‘target’ molecules can be efficiently created depends on the number of ‘tools’ utilized by chemists.” said Prof. Gong Chen.

Chen’s team applied a hypervalent iodine reagent in the new organic synthetic method, which can achieve efficient configuration flipping of various cyclic alkane compounds under very mild and easy reaction condition. Related mechanism reveals that azide radical, as the receptor of a hydrogen atom, can transfer the hydrogen atom back and forth between tertiary carbon atoms.

Researchers introduced that this method has been successfully applied in the configuration flipping of steroid compound, which enjoys a promising application prospect in the configuration transformation of complex natural products. Moreover, it could also achieve the exchange between the hydrogen atoms and their isotopes in compounds, breaking new ground for the preparation of isotope labeled molecule widely applied in biomedicine.

Link to: https://pubs.acs.org/doi/10.1021/jacs.8b05753

Source: Nankai News

Written by Junhui Wu

Edited by Yuchen Shi




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