Efficient biotransformations in Cunninghamella elegans and Streptomyces sp. JCM9888 of selectively fluorinated benzoic acids to the corresponding benzamides and benzyl alcohols

Abstract

An efficient conversion of ortho, meta and para fluoro- and trifluoromethyl-substituted benzoic acids to the corresponding benzamides in fermentations of the soil bacterium Streptomyces sp. JCM9888 is described. We also report the efficient reduction of the same class of substrates to the corresponding benzyl alcohols with the fungi Cunninghamella elegans. These biotransformations were surprisingly efficient and may have value as disruptive technologies in process chemistry.

Graphical Abstract

Keywords:

• Biotransformations
• Streptomyces sp. JCM9888
• Cunninghamella elegans DSM1908
• benzoic acids
• benzamides
• benzyl alcohols

Acknowledgements

We are grateful to the Commonwealth Scholarship Commission and also the Royal Society of Chemistry for their support. We are also extremely grateful to Prof Cormac D. Murphy of University College Dublin for a strain of C. elegans.

Author contributions

Oluwayinka O. Oke designed and performed the microbiology and synthesis experiments and helped develop the manuscript. Yawen Chen assisted with the microbiology aspects of the project. Chukwuemeka Isanbor and Olayinka T. Asekun guided the research and assisted in funding support. David O’Hagan led the project, guided the research and drafted the manuscript.

Disclosure statement

The authors report there are no conflicts of interest.

Additional information

Funding

Support was received from the Commonwealth Scholarship Council for a Split Site Studentship (OO) and also from the Royal Society of Chemistry for a travel Grant (C.I). This is gratefully acknowledged.