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Biotransformation of C20- and C22-polyunsaturated fatty acids and fish oil hydrolyzates to R,R-dihydroxy fatty acids as lipid mediators using double-oxygenating 15R-lipoxygenase
- Title
- Biotransformation of C20- and C22-polyunsaturated fatty acids and fish oil hydrolyzates to R,R-dihydroxy fatty acids as lipid mediators using double-oxygenating 15R-lipoxygenase
- Authors
- Lee; Jin; Ko; Yoon-Joo; Park; Jin-Byung; Oh; Deok-Kun
- Ewha Authors
- 박진병
- SCOPUS Author ID
- 박진병
![scopus](/images/layout/icon2.png)
- Issue Date
- 2024
- Journal Title
- Green Chemistry
- ISSN
- 1463-9262
- Citation
- Green Chemistry vol. 26, no. 8, pp. 4665 - 4676
- Publisher
- Royal Society of Chemistry
- Indexed
- SCIE; SCOPUS
![scopus](/images/layout/scopus2.gif)
- Document Type
- Article
- Abstract
- C20- and C22-dihydroxy fatty acids (DiHFAs) are bioactive lipid mediators (LMs) in humans. Among them, leukotrienes are inflammatory mediators, whereas resolvins generated by M2 macrophages in humans are anti-inflammatory mediators. However, the synthesis of LMs by chemical or biological methods is inefficient. Here, we discovered a double-oxygenating arachidonate (ARA) 15R-lipoxygenase (15R-LOX) with the highest catalytic activity among the reported ARA LOXs. Cells expressing double-oxygenating 15R-LOX converted ARA, eicosapentaenoic acid, and docosahexaenoic acid (DHA) and DHA-rich fish oil hydrolyzates into 5R,15R-dihydroxyeicosatetraenoic acid, 5R,15R-dihydroxyeicosapentaenoic acid, and 7R,17R-dihydroxydocosahexaenoic acid as isomers of leukotriene B4, resolvin E4, and resolvin D5, which were identified as new compounds, within 1.5 h, with concentrations >1.5 g L−1, conversions >77% (w/w), and productivity >1.0 g L−1 h−1, respectively. Double-oxygenating 15R-LOX was altered to single-oxygenating 15R-LOX by the L606F mutation using structure-guided engineering. Cells expressing single-oxygenating 15R-LOX produced 15R-hydroxyeicosatetraenoic acid, 15R-hydroxyeicosapentaenoic acid, and 17R-hydroxydocosahexaenoic acid, respectively. These results demonstrated that the six medicinally important LMs could be prepared from C20- and C22-polyunsaturated fatty acids and inexpensive DHA-rich fish oil hydrolyzates by cost-effective, eco-friendly, and efficient biosynthesis using the discovered double-oxygenating and engineered single-oxygenating LOXs. © 2024 The Royal Society of Chemistry.
- DOI
- 10.1039/d4gc00308j
- Appears in Collections:
- 공과대학 > 식품생명공학과 > Journal papers
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