Biotransformation of eicosapentaenoic acid into the dihydroxyeicosapentaenoic acids resolvin E4 and its enantiomer by 15S- and 15R-lipoxygenases expressed in Escherichia coli

Abstract

Objectives To enhance the production of resolvin E4 (RvE4) or its enantiomer from eicosapentaenoic acid (EPA), Archangium violaceum 15S-lipoxygenase (15S-LOX) or Sorangium cellulosum 15R-LOX was expressed in Escherichia coli with solvent, polymer, and adsorbent resin, respectively. Results The concentrations of cells and substrate and the types and concentrations of solvent, polymer, and resin were optimized for the biotransformation of EPA into RvE4 (5S,15S-dihydroxyeicosapentaenoic acid) and its enantiomer (5R,15R-dihydroxyeicosapentaenoic acid). Under optimized conditions, A. violaceum 15S-LOX and S. cellulosum 15R-LOX expressed in E. coli converted 6.0 mM (1.8 g L−1) EPA into 4.3 mM (1.4 g L−1) RvE4 and 5.8 mM (1.9 g L−1) RvE4 enantiomer in 60 min, with productivities of 4.3 and 5.8 mM h−1 and molar conversions of 72 and 97%, respectively. The concentrations of RvE4 and its enantiomer resulting from the conversion of EPA with solvent, polymer, and resin were 3.1- and 5.3-fold higher than those without additives, respectively. Conclusions The concentrations, productivities, and conversions of RvE4 and its enantiomer were increased by optimizing the concentrations of cells and substrate and the types and concentrations of solvent, polymer, and adsorbent resin.