Chemoenzymatic Cascade Conversion of Linoleic Acid into a Secondary Fatty Alcohol Using a Combination of 13 S-Lipoxygenase, Chemical Reduction, and a Photo-Activated Decarboxylase

Hee Jeong Cha, Hyo Ran Lee, Jinwon Lee, Deok Kun Oh, Jin Byung Park

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

Linoleic acid serves as a starting material in the production of various oleochemicals. Here, we have investigated the transformation of linoleic acid into 13S-hydroxy-(9Z,11E)-octadecadienoic acid (13-HOD) (17) and 6S-hydroxy-(7E,9Z)-heptadecadiene (6-HHD) (18) by using 13S-lipoxygenase from Pseudomonas aeruginosa (Pa-LOX) and photo-activated decarboxylase from Chlorella variabilis NC64A (Cv-FAP). Remarkably, the recombinant Escherichia coli expressing Pa-LOX was able to produce 13S-hydroperoxy-(9Z,11E)-octadecadienoic acid (16) at a maximum rate of 850 μmol/g dry cells/min. This allowed the accumulation of 13-HOD (17) to 161 mM (48 g/L) concentration from 200 mM linoleic acid in the reaction medium within 3.5 h. We have also demonstrated that the fatty acids, including CC bonds in cis- and trans-forms [e.g., 13-HOD (17)], were subjected to photo-activated decarboxylation by Cv-FAP. Ultimately, the secondary fatty alcohol [i.e., 6-HHD (18)] was produced from linoleic acid through the chemo/enzymatic cascade transformation, consisting of dioxygenation of linoleic acid by intracellular Pa-LOX and reduction of the hydroperoxy fatty acid (16) by Tris(2-carboxyethyl) phosphine or cysteine. Moreover, the photo-activated decarboxylation of the hydroxy fatty acid (17) by intracellular Cv-FAP achieved a conversion of ca. 74% in a one-pot process. This study will contribute to the valorization of γ-linolenic and arachidonic acid, as well as linoleic acid, which are the substrates of Pa-LOX.

Original languageEnglish
Pages (from-to)10837-10845
Number of pages9
JournalACS Sustainable Chemistry and Engineering
Volume9
Issue number32
DOIs
StatePublished - 16 Aug 2021

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MEST) (no. 2020R1A2B5B03002376) and the C1 Gas Refinery Research Center (NRF grant number: 2018M3D3A1A01055735) of the NRF funded by the Ministry of Science and ICT.

Publisher Copyright:
© 2021 American Chemical Society.

Keywords

  • 13 S-hydroxy-(9 Z,11 E)-octadecadienoic acid
  • 13 S-lipoxygenase
  • 6 S-hydroxy-(7 E,9 Z)-heptadecadiene
  • linoleic acid
  • photo-activated decarboxylase

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