Removing the Obstacle to (-)-Menthol Biosynthesis by Building a Microbial Cell Factory of (+)-cis-Isopulegone from (-)-Limonene

ChemSusChem. 2022 May 6;15(9):e202101741. doi: 10.1002/cssc.202101741. Epub 2021 Oct 13.

Abstract

Microbial synthesis of plant-based (-)-menthol is of great interest because of its high demand (≈30 kiloton per year) as well as unique odor and cooling characteristics. However, this remains a great challenge due to the yet unfilled gap between (-)-limonene and (+)-cis-isopulegone. Herein, the first artificial and effective system was developed for (+)-cis-isopulegone biosynthesis from (-)-limonene by recruiting two bacterial enzymes to replace their inefficient counterparts from Mentha piperita, limonene-3-hydroxylase, and isopiperitenol dehydrogenase. A cofactor self-regenerative recombinant Escherichia coli strain was constructed by introducing a formate dehydrogenase for nicotinamide adenine dinucleotide phosphate (NADPH) regeneration and an engineered microbial isopiperitenol dehydrogenase. The production of (+)-cis-isopulegone (up to 281.2 mg L-1 ) was improved by 36 times compared with that of the initial strain. This work lays a reliable foundation for the microbial synthesis of (-)-menthol.

Keywords: biocatalysis; biosynthesis; enzyme catalysis; microbial cell factory; oxidoreductases.

MeSH terms

  • Cyclohexane Monoterpenes
  • Limonene
  • Mentha piperita*
  • Menthol*

Substances

  • Cyclohexane Monoterpenes
  • Menthol
  • pulegone
  • Limonene