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Biocatalytic conversion of epoxides
Erik J de Vries1, Dick B Janssen
1Department of Biochemistry, Groningen Biomolecular Sciences & Biotechnology Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
Current Opinion in Biotechnology
|August 29, 2003
Summary
Chiral compounds can be produced using epoxides via biocatalysis. Enzymatic reactions like epoxide hydrolase and haloalcohol dehalogenases offer green chemistry routes to enantiopure products.
Area of Science:
- Biocatalysis and Green Chemistry
Background:
- Epoxides are versatile chiral intermediates in chemical synthesis.
- Biocatalytic transformations of epoxides are crucial for producing enantiopure compounds.
Purpose of the Study:
- To review and highlight the enzymatic methods for enantioselective epoxide conversion.
- To discuss the catalytic mechanisms and scope of different biocatalytic reactions involving epoxides.
Main Methods:
- Enzymatic kinetic resolution using epoxide hydrolases.
- Enantioconvergent enzymatic hydrolysis of epoxides.
- Non-hydrolytic enantioselective ring opening catalyzed by haloalcohol dehalogenases.
Main Results:
- Epoxide hydrolases yield diols and enantiopure substrates through kinetic resolution.
- Enzymatic hydrolysis provides high yields of single enantiomers from racemic epoxides.
- Haloalcohol dehalogenases enable enantioselective ring opening with various nucleophiles.
Conclusions:
- Distinct catalytic mechanisms (covalent vs. non-covalent) dictate the scope of enzymatic epoxide conversions.
- Biocatalytic routes for epoxides are expanding, enhancing their significance in green chemistry.