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Updated: Nov 4, 2025
07:59
A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
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Simple Plug-In Synthetic Step for the Synthesis of (-)-Camphor from Renewable Starting Materials
Elia Calderini1, Ivana Drienovská1, Kamela Myrtollari1,2
1Institute of Molecular Biotechnology, Graz University of Technology, Petersgasse 14, 8010, Graz, Austria.
Chembiochem : a European Journal of Chemical Biology
|May 25, 2021
Summary
Enzymes like cephalosporin Esterase B and Esterase C enable efficient production of optically pure camphor and isoborneol isomers. This method utilizes readily available industrial byproducts, offering a sustainable route to valuable monoterpenols.
Area of Science:
- Biocatalysis and enzyme engineering
- Organic synthesis and green chemistry
- Natural product chemistry
Background:
- Racemic camphor and isoborneol are industrial byproducts, while optically pure (1S)-camphor is scarce.
- Current synthesis of camphor from α-pinene involves racemic intermediates, complicating access to pure isomers.
- Enantioselective hydrolysis of isobornyl esters presents a potential strategy for obtaining optically pure monoterpenols.
Purpose of the Study:
- To investigate the enantioselective hydrolysis of racemic monoterpenol esters using lipases and esterases.
- To identify enzymes capable of efficiently resolving isobornyl esters for the synthesis of optically pure isoborneol and camphor.
- To explore the integration of enzymatic kinetic resolution into existing industrial processes for camphor production.
Main Methods:
- Screening of commercial lipases and esterases for enantioselectivity in resolving racemic monoterpenols.
- Enzymatic kinetic resolution of racemic isobornyl butyrate using selected esterases.
- Optimization of substrate acyl chain length to enhance enantioselectivity.
- Integration of the resolution process into the α-pinene to camphor production pathway.
Main Results:
- Commercial lipases and esterases showed limited enantioselectivity.
- Cephalosporin Esterase B (EstB) from Burkholderia gladioli and Esterase C (EstC) from Rhodococcus rhodochrous exhibited outstanding enantioselectivity (E>100) for butyryl esters of isoborneol, borneol, and fenchol.
- Enantioselectivity increased with longer acyl chain lengths of the substrate.
- The kinetic resolution of isobornyl butyrate was successfully integrated into camphor synthesis from α-pinene.
Conclusions:
- EstB and EstC are highly effective biocatalysts for the enantioselective synthesis of optically pure monoterpenols.
- Enzymatic kinetic resolution provides a facile and sustainable method for accessing valuable camphor and isoborneol isomers from renewable resources.
- This approach offers a significant improvement over traditional methods for obtaining optically pure monoterpenols.
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