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Hydrogen-Borrowing Alcohol Bioamination with Coimmobilized Dehydrogenases
Wesley Böhmer1, Tanja Knaus1, Francesco G Mutti1
1Van't Hoff Institute for Molecular Sciences, HIMS-Biocat University of Amsterdam Science Park 904, 1098 XH Amsterdam (The Netherlands).
Chemcatchem
|March 9, 2018
Summary
This study enhances biocatalytic amination of alcohols using co-immobilized alcohol dehydrogenase (ADH) and amine dehydrogenase (AmDH) enzymes. The improved dual-enzyme system demonstrates high efficiency, recyclability, and excellent enantioselectivity for chiral amine production.
Area of Science:
- Biocatalysis
- Organic Chemistry
- Enzyme Engineering
Background:
- Alcohol amination is a key chemical transformation.
- Redox-neutral (hydrogen-borrowing) asymmetric amination typically requires combining alcohol dehydrogenase (ADH) and amine dehydrogenase (AmDH).
Purpose of the Study:
- To enhance the efficiency and recyclability of hydrogen-borrowing biocatalytic amination.
- To develop a robust dual-enzyme system for asymmetric alcohol amination.
Main Methods:
- Co-immobilization of ADH and AmDH onto controlled porosity glass Fe(III) ion-affinity beads.
- Testing the dual-enzyme system for the amination of various (S)-configured alcohol substrates.
Main Results:
- Demonstrated recyclability of the dual-enzyme system over 5 cycles.
- Achieved high total turnover numbers (>4000 for ADH, >1000 for AmDH).
- Obtained up to 95% conversion and >99% enantiomeric excess (ee) for (S)-configured alcohol substrates.
- Achieved 90% conversion and 80% yield in preparative-scale amination of (S)-phenylpropan-2-ol within 24 hours.
Conclusions:
- Co-immobilization significantly enhances the efficiency of hydrogen-borrowing biocatalytic amination.
- The developed dual-enzyme system is highly recyclable and effective for producing chiral amines from alcohols with excellent enantioselectivity.
- This approach offers a sustainable and efficient method for synthesizing valuable chiral amine products.
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