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. 2020 Nov 2;10:18849. doi: 10.1038/s41598-020-76005-5

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© The Author(s) 2020

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.

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RP-HPLC analysis of epoxide ring-opened products by sodium hydroxide (NaOH). (a) Purified 7S,15R-dihydroxy-16S,17S-epoxy-docosapentaenoic acid as a precursor. (b) Two products were generated by NaOH: main product was 7S,15R,16S,17S-tetrahydroxy docosapentaenoic acid (conversion rate of 90% or less) and minor product was RvD2 (conversion rate of 10%). (c) Tetrahydroxy fatty acid was produced by epoxide hydrolase (EH; commercially available) to use as a reference. (d) RvD2 standard. The epoxide ring-opening reaction was performed with NaOH at 30 °C overnight.