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

2 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

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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