Biological stereoselective reduction of 4-methylcyclohexanone and 4-ethylcyclohexanone by anthracnose fungi

• Published in: Journal of chemical technology and biotechnology (1986) Vol. 75; no. 2; pp. 143 - 146
• Main Authors: Miyazawa, M, Okamura, S, Yamaguchi, M, Kameoka, H
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.02.2000; Wiley
• Subjects: 4-ethylcyclohexanone; 4-methylcyclohexanone; Alcohols; anthracnose fungi; Aromatic hydrocarbons; Biocatalysts; Bioconversions. Hemisynthesis; Biological and medical sciences; biological stereoselective reduction; Biotechnology; biotransformation; Catalyst selectivity; Colletotrichum; Fundamental and applied biological sciences. Psychology; Fungi; Glomerella cingulata; metabolism; Methods. Procedures. Technologies; Reduction; Stereochemistry; Fungi; Chemical reduction; Stereoselectivity; Biotransformation; Ascomycetes; Fungi Imperfecti; Glomerella cingulata; Colletotrichum; Ketone; Thallophyta
• ISSN: 0268-2575; 1097-4660
• DOI: 10.1002/(SICI)1097-4660(200002)75:2<143::AID-JCTB195>3.0.CO;2-Z

The biotransformations of 4‐methylcyclohexanone and 4‐ethylcyclohexanone were investigated using 10 kinds of anthracnose fungi as biocatalysts. 4‐Methylcyclohexanone and 4‐ethylcyclohexanone were reduced to the corresponding cis‐ and trans‐alcohols respectively. In the case of 4‐methylcyclohexanone, it was transformed to mainly trans‐4‐methylcyclohexanol by all the fungi examined. In particular, the ratio of cis‐ and trans‐alcohol products was shown to be 1:81 with high stereoselectivity by Colletotrichum lagenarium after a 7‐day incubation period. The biotransformation of 4‐ethylcyclohexanone by C lagenarium, C dematium MAFF410046, C trifolii MAFF305389, C fragariae, C atramentarium MAFF712102, C lindemuthianum (C‐1), C lindemuthianum (C‐3) and C lindemuthianum (C‐13) produced mainly trans‐4‐ethylcyclohexanol. On the other hand, cis‐alcohol was formed with stereoselectivity by Glomerella cingulata and C graminicola MAFF305460. © 2000 Society of Chemical Industry