H2O2-driven enzymatic oxyfunctionalization of tertiary C-H bonds
Yawen Huang1,2, Huanhuan Li3, Pengpeng Zhang1,2
1University of Chinese Academy of Sciences, Beijing 100049, China.
Chemical Communications (Cambridge, England)
|July 7, 2023
Summary
The Agrocybe aegerita peroxygenase enzyme selectively hydroxylates tertiary C-H bonds, producing valuable alcohols and related compounds with high efficiency. This enzymatic approach offers a streamlined method for late-stage functionalization of drug molecules.
Area of Science:
- Biocatalysis
- Organic Chemistry
- Enzymology
Background:
- Tertiary C-H bond hydroxylation is challenging in organic synthesis.
- Enzymatic catalysis offers selective and efficient alternatives.
Purpose of the Study:
- To investigate the utility of Agrocybe aegerita peroxygenase for selective C-H bond hydroxylation.
- To explore its application in late-stage functionalization of complex molecules.
Main Methods:
- Utilized purified peroxygenase from Agrocybe aegerita.
- Performed hydroxylation reactions on various substrates with tertiary C-H bonds.
Main Results:
- Achieved regioselective hydroxylation of tertiary C-H bonds.
- Obtained tertiary alcohols, diols, and ketols with good to high yields and turnover numbers.
- Demonstrated successful late-stage functionalization of drug molecules.
Conclusions:
- Agrocybe aegerita peroxygenase is a powerful biocatalyst for selective tertiary C-H hydroxylation.
- This enzymatic method provides a streamlined route to valuable compounds and facilitates drug discovery.
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