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Atroposelective Synthesis of Styrenes by Alcohol-Dehydrogenase-Catalyzed Dynamic Kinetic Resolution.
Meiting Zhou1, Yan Chen1, Shuai Liu1
1Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, China.
Researchers developed a new enzymatic method for synthesizing chiral styrenes. This dynamic kinetic resolution uses engineered alcohol dehydrogenase to create valuable atropisomeric compounds with high selectivity and yield.
Area of Science:
- Organic Chemistry
- Biocatalysis
- Enzyme Engineering
Background:
- Atropisomeric styrenes are important chiral building blocks.
- Their synthesis often requires complex methods.
Purpose of the Study:
- To develop an efficient and stereoselective method for synthesizing atropisomeric styrenes.
- To utilize enzyme engineering for enhanced catalytic activity.
Main Methods:
- Employed alcohol dehydrogenase from Ralstonia sp.
- Utilized a structure-guided protein engineering approach.
- Performed atroposelective dynamic kinetic resolution.
Main Results:
- Achieved highly stereoselective synthesis of axially chiral styrenes (R and S configurations).
- Obtained high yields (up to 99%) and enantiomeric excess (up to 98%).
- Identified a reconfigured proton relay network in specific enzyme variants responsible for stereoinversion.
Conclusions:
- Developed a novel enzymatic strategy for synthesizing challenging atropisomeric scaffolds.
- Demonstrated the power of enzyme engineering in biocatalysis.
- Provided a valuable tool for stereocontrolled synthesis.
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