Production of 8,11‐dihydroxy and 8‐hydroxy unsaturated fatty acids from unsaturated fatty acids by recombinant Escherichia coli expressing 8,11‐linoleate diol synthase from Penicillium chrysogenum

Abstract

Hydroxy unsaturated fatty acids can be used as antimicrobial surfactants. 8,11-Linoleate diol synthase (8,11-LDS) catalyzes the conversion of unsaturated fatty acid to 8-hydroperoxy unsaturated fatty acid, and it is subsequently isomerized to 8,11-dihydroxy unsaturated fatty acid by the enzyme. The optimal reaction conditions of recombinant Escherichia coli expressing Penicillium chrysogenum 8,11-LDS for the production of 8,11-dihydroxy-9,12(Z,Z)-octadecadienoic acid (8,11-DiHODE), 8,11-dihydroxy-9,12,15(Z,Z,Z)-octadecatrienoic acid (8,11-DiHOTrE), 8-hydroxy-9(Z)-hexadecenoic acid (8-HHME), and 8-hydroxy-9(Z)-octadecenoic acid (8-HOME) were pH 7.0, 25°C, 10 g/L linoleic acid, and 20 g/L cells; pH 6.0, 25°C, 6 g/L α-linolenic acid, and 60 g/L cells; pH 7.0, 25°C, 8 g/L palmitoleic acid, and 25 g/L cells; and pH 8.5, 30°C, 6 g/L oleic acid, and 25 g/L cells, respectively. Under these optimized conditions, the recombinant cells produced 6.0 g/L 8,11-DiHODE for 60 min, with a conversion of 60% (w/w) and a productivity of 6.0 g/L/h; 4.3 g/L 8,11-DiHOTrE for 60 min, with a conversion of 72% (w/w) and a productivity of 4.3 g/L/h; 4.3 g/L 8-HHME acid for 60 min, with a conversion of 54% (w/w) and a productivity of 4.3 g/L/h; and 0.9 g/L 8-HOME for 30 min, with a conversion of 15% (w/w) and a productivity of 1.8 g/L/h. To best of our knowledge, this is the first report on the biotechnological production of 8,11-DiHODE, 8,11-DiHOTrE, 8-HHME, and 8-HOME. © 2017 American Institute of Chemical Engineers Biotechnol. Prog., 33:390-396, 2017.

Production of 6,8‐Dihydroxy Fatty Acids by Recombinant Escherichia coli Expressing T879A Variant 6,8‐Linoleate Diol Synthase from Penicillium oxalicum

“…S1, Supporting Information), while the maximum activity of the purified enzyme was observed at pH 6.5 and 25°C (Seo et al, ). Activities for the biotransformation of linoelic acid into DiHODE by recombinant E. coli expressing 5,8‐LDS from A. nidulans (Seo et al, ), 7,8‐LDS from G. cingulate (Seo et al, ), and 8,11‐LDS from P. chrysogenum (Kim et al, ) have been shown to be maximal at pH 7.5 and 35°C, pH 7.0 and 19°C, and pH 7.0 and 25°C, respectively. Thermal stability was evaluated by determining residual enzyme activity after pre‐incubation for 30 min at temperatures ranging from 20 to 45°C (Fig.…”

“…A diverse range of DiHFA have been produced by recombinant Escherichia coli cells. These include 5,8‐dihydroxy‐9( Z )‐octadecenoic acid (5,8‐DiHOME), 5,8‐dihydroxy‐9,12( Z , Z )‐octadecadienoic acid (5,8‐DiHODE), and 5,8‐dihydroxy‐9,12,15( Z , Z , Z )‐octadecatrienoic acid (5,8‐DiHOTrE) produced by recombinant E. coli expressing 5,8‐LDS from A. nidulans (Seo et al, ); 7,8‐DiHOME, 7,8‐DiHODE, and 7,8‐DiHOTrE by cells expressing 7,8‐LDS from Glomerella cingulate (Seo et al, ); and 8,11‐DiHODE and 8,11‐DiHOTrE by cells expressing 8,11‐LDS from Penicillium chrysogenum (Kim et al, ). Recombinant E. coli has been used for DiHFA production because cell reactions are more stable and economical than enzymatic reactions (Sim et al, ).…”

Production of 8,11‐dihydroxy fatty acids from oleic and palmitoleic acids by Escherichia coli cells expressing variant 6,8‐linoleate diol synthases from Penicillium oxalicum

“…However, the recombinant cells convert oleic and palmitoleic acids into 8‐HPOME and 8‐hydroperoxy‐9( Z )‐hexadecenoic acid (HPHME) only, respectively, without further catalytic reactions due to the substrate specificity of 8,11‐LDS from P . chrysogenum 30 . Thus, 8,11‐LDS from P .…”

Liquid lipase‐catalyzed hydrolysis of gac oil for fatty acid production: Optimization using response surface methodology

“…Fatty acids have attracted considerable attention due to their various industrial applications such as in manufacturing surfactants, soaps, food products, and various biomedical applications . In addition, the conversion of fatty acids into biodiesel through esterification with alcohol has gained the interest of researchers worldwide as biodiesel is considered to be an alternative to petrodiesel to solve the shortage of fossil fuels and environmental concerns .…”