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Biotransformation of (+/-)-2-methylcyclohexanone by fungi
Mai Kawamoto1, Takamitsu Utsukihara, Chika Abe
1Department of Chemistry, Rikkyo (St. Paul's) University, 3-34-1 Nishi-Ikebukuro, Toshima-ku, Tokyo 171-8501, Japan.
Biotechnology Letters
|April 23, 2008
Summary
This study explored fungal biotransformation of 2-methylcyclohexanone, with Fusarium sp. proving effective for oxidoreduction and Baeyer-Villiger oxidation, yielding specific alcohols and lactones.
Area of Science:
- Biotechnology and Biocatalysis
- Organic Chemistry
- Microbial Transformation
Background:
- 2-Methylcyclohexanone is a cyclic ketone with potential applications in organic synthesis.
- Microbial biotransformation offers a sustainable approach for chemical modifications.
- Investigating fungal strains for selective oxidation and reduction reactions is crucial for green chemistry.
Purpose of the Study:
- To investigate the biotransformation potential of various fungal strains and mushroom cultures on 2-methylcyclohexanone.
- To identify effective biocatalysts for oxidoreduction and Baeyer-Villiger oxidation of the target substrate.
- To characterize the stereochemical outcomes of the biotransformation reactions.
Main Methods:
- Screening of 16 fungal strains and mushroom cultures for biotransformation activity.
- Incubation of 2-methylcyclohexanone with selected biocatalysts under optimized conditions.
- Analysis of reaction products using chromatographic and spectroscopic techniques to determine yield and enantiomeric excess.
Main Results:
- Fusarium sp. demonstrated significant biocatalytic activity for the oxidoreduction of 2-methylcyclohexanone.
- cis-2-Methylcyclohexanol was isomerized to trans-2-methylcyclohexanol by Fusarium sp.
- Baeyer-Villiger oxidation of 2-methylcyclohexanone using Fusarium sp. AP-2 yielded the corresponding lactone with 46% yield and 94% enantiomeric excess.
Conclusions:
- Fusarium sp. is an effective biocatalyst for the stereoselective transformation of 2-methylcyclohexanone.
- The study highlights the potential of microbial oxidation for producing valuable chiral intermediates like lactones.
- This research contributes to the development of greener synthetic routes in organic chemistry.
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