Epicoccum sorghinum: A promising biocatalyst for obtainment of (1R,2S,4R)-neodihydrocarveol by selective bioreduction of (4R)-(−)-carvone

• Published in: Biocatalysis and agricultural biotechnology 2020-10, Vol.29, p.101809, Article 101809
• Main Authors: de O. Souza, Felipe, Ferrarezi, Arthur A., dos Santos, Rogério A.M., da Silva, Michael J.V., Rosa, Fernanda A., Castro, Juliana C., Polonio, Julio C., Pamphile, João A., Gonçalves, José E., de Oliveira, Arildo J.B., Gonçalves, Regina A.C.
• Format: Article
• Language: English
• Subjects: [BMIM][BF4]; Ene reductase; Epicoccum sorghinum; Keto reductase; Neodihydrocarveol
• ISSN: 1878-8181; 1878-8181
• DOI: 10.1016/j.bcab.2020.101809

Biocatalysis represents an efficient and versatile tool for organic synthesis and green chemistry, since enzymes can perform many chemical transformations with advantages over their chemical counterparts. (4R)-(−)-carvone and its reduced derivatives are natural products with biological and industrial applications, specially (1R,2S,4R)-neodihydrocarveol, due to its pharmacological properties, as well as fragrances supplies. Dialkyl imidazolium-based ionic liquids (ILs) are known to be useful in biocatalytic processes due to their unique physico-chemical properties, low toxicity and ability to improve enzymatic activity. In the present study, we describe the bioreduction of (4R)-(−)-carvone using a filamentous fungus isolated from human skin, molecularly identified by MLSA as Epicoccum sorghinum, and ionic liquid (IL) 1-butyl-3-methyl-imidazolium tetrafluoroborate ([BMIM][BF4]), as co-solvent. The addition of 0.2% (v/v) of [BMIM][BF4] favoured the bioreduction of the substrate (4R)-(−)-carvone at a concentration of 0.198 mmol, affording 65% of the major compound (1R,2S,4R)-neodihydrocarveol, with diastereomeric excess greater than 99% after 18 h of biocatalytic reaction. Also, the isolated product was obtained with an appreciable yield of 59% after column chromatography. [Display omitted] •Epicoccum sorghinum was able to produce (1R,2S,4R)-neodihydrocarveol selectively.•Selective bioreduction of (4R)-carvone using ionic liquid [BMIM][BF4] as co-solvent.•[BMIM][BF4] was able to improve conversion and stereosselectivity•The reaction was performed in a multi-step one-pot fashion.