Related Experiment Videos
Epoxide hydrolases and their synthetic applications
R V Orru1, A Archelas, R Furstoss
1Institute of Organic Chemistry, Graz University of Technology, Austria.
Advances in Biochemical Engineering/Biotechnology
|February 6, 1999
Summary
Enzyme-catalyzed epoxide hydrolysis by epoxide hydrolases yields chiral 1,2-diols for drug synthesis. These biocatalysts, found in bacteria and fungi, offer efficient asymmetric synthesis routes beyond traditional methods.
Area of Science:
- Biocatalysis
- Organic Synthesis
- Enzymology
Background:
- Chiral epoxides and 1,2-diols are crucial for synthesizing bioactive compounds.
- Epoxide hydrolases catalyze enantioselective epoxide hydrolysis, producing these chiral building blocks.
- These enzymes are more widespread in bacteria and fungi than previously known.
Purpose of the Study:
- To explore the use of epoxide hydrolases for asymmetric synthesis.
- To identify microbial sources of effective epoxide hydrolases.
- To demonstrate methods for obtaining optically pure diols with high yields.
Main Methods:
- Enzymatic hydrolysis of epoxides using epoxide hydrolases from bacteria (e.g., Rhodococcus, Nocardia) and fungi (e.g., Aspergillus, Beauveria).
- Utilizing SN2-specific epoxide ring opening to form trans-configured 1,2-diols.
- Employing non-natural nucleophiles like azides and amines to synthesize azido- and amino-alcohols.
Main Results:
- Identification of diverse bacterial and fungal sources of epoxide hydrolases with excellent enantioselectivities.
- Demonstration of methods yielding optically pure diols significantly exceeding the 50% mark of classic kinetic resolutions.
- Successful synthesis of enantiomerically enriched vicinal azido- and amino-alcohols.
Conclusions:
- Epoxide hydrolases are versatile biocatalysts for the asymmetric synthesis of valuable chiral compounds.
- Microbial epoxide hydrolases provide efficient and scalable routes to enantiopure epoxides and diols.
- These enzymes enable the preparation of complex biologically active molecules through innovative synthetic strategies.