Solvent-induced 7R-dioxygenase activity of soybean 15-lipoxygenase-1 in the formation of omega-3 DPA-derived resolvin analogs

Dobson, Eleanor P.; Barrow, Colin J.; Adcock, Jacqui L.

doi:10.1016/j.molcatb.2014.07.007

Cited by 3 publications

(2 citation statements)

References 57 publications

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“…The stereoconfiguration of DiHFAs was confirmed by comparison with the reported NMR spectroscopy. NMR results for the reaction products 7,17-DiHDoHE and 7,17-DiHDoPE were the same as those of the known 7 S ,17 S -DiHDoHE and 7 S ,17 S -DiHDoPE . The identification of these products explained that we discovered a microbial enzyme to synthesize SPMs from PUFAs.…”

Section: Resultssupporting

confidence: 67%

“…NMR results for the reaction products 7,17-DiHDoHE and 7,17-DiHDoPE were the same as those of the known 7S,17S-DiHDoHE 31 and 7S,17S-DiHDoPE. 32 The identification of these products explained that we discovered a microbial enzyme to synthesize SPMs from PUFAs. The detailed explanation for the identification of all LMs in the present study is included in Supporting Information.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Discovery and Engineering of a Microbial Double-Oxygenating Lipoxygenase for Synthesis of Dihydroxy Fatty Acids as Specialized Proresolving Mediators

Liu

Kim

et al. 2020

ACS Sustainable Chem. Eng.

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Specialized proresolving mediators (SPMs), such as resolvins and maresins, resolve inflammation and protect against infection at trace amounts generated by neutrophils and macrophages in humans. Thus, SPMs have been leading compounds in treatment of inflammation and infection. These mediators have been synthesized using chemical methods, which have disadvantages such as use of toxic chemical reagents, many (20−30) step reactions, and expensive processes. Here, we first discovered a human SPM-producing microorganism and found a 15-lipoxygenase (15-LOX) from the microorganism that produces SPMs via double oxygenation from polyunsaturated fatty acids. The 15-LOX was altered to 12-LOX using structure-based engineering. We performed the quantitative biocatalytic synthesis of SPMs by wild-type 15-LOX and engineered 12-LOX. Owing to the high double-oxygenating activities of LOXs, we succeeded in the one-enzyme biotransformation of docosahexaenoic acid and docosapentaenoic acid into the SPM resolvin D5 (RvD5, 7S,17S-dihydroxydocosahexaenoic acid) and RvD5 n−3 DPA (7S,17Sdihydroxydocosapentaenoic acid) (>40% conversion), respectively, by Escherichia coli expressing wild-type 15-LOX and into the 7Sepimer of maresin (MaR) 1 (7S,14S-dihydroxydocosahexaenoic acid) and 7S-epimer of MaR1 n−3 DPA (7S,14S-dihydroxydocosapentaenoic acid) (>20% conversion), respectively, by E. coli expressing engineered 12-LOX. Our study contributes to the environmentally friendly synthesis of medicinally important SPMs.

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Section: Resultssupporting

confidence: 67%

Section: ■ Results and Discussionmentioning

confidence: 99%