View : 419 Download: 0
Chemoenzymatic Cascade Conversion of Linoleic Acid into a Secondary Fatty Alcohol Using a Combination of 13S-Lipoxygenase, Chemical Reduction, and a Photo-Activated Decarboxylase
- Title
- Chemoenzymatic Cascade Conversion of Linoleic Acid into a Secondary Fatty Alcohol Using a Combination of 13S-Lipoxygenase, Chemical Reduction, and a Photo-Activated Decarboxylase
- Authors
- Cha, Hee-Jeong; Lee, Hyo-Ran; Lee, Jinwon; Oh, Deok-Kun; Park, Jin-Byung
- Ewha Authors
- 박진병
- SCOPUS Author ID
- 박진병
- Issue Date
- 2021
- Journal Title
- ACS SUSTAINABLE CHEMISTRY & ENGINEERING
- ISSN
- 2168-0485
- Citation
- ACS SUSTAINABLE CHEMISTRY & ENGINEERING vol. 9, no. 32, pp. 10837 - 10845
- Keywords
- linoleic acid; 13S-hydroxy-(9Z, 11E)-octadecadienoic acid; 6S-hydroxy-(7E, 9Z)-heptadecadiene; 13S-lipoxygenase; photo-activated decarboxylase
- Publisher
- AMER CHEMICAL SOC
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- 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 mu mol/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 C=C 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 photoactivated 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 gamma-linolenic and arachidonic acid, as well as linoleic acid, which are the substrates of Pa-LOX.
- DOI
- 10.1021/acssuschemeng.1c03136
- Appears in Collections:
- 공과대학 > 식품생명공학과 > Journal papers
- Files in This Item:
There are no files associated with this item.
- Export
- RIS (EndNote)
- XLS (Excel)
- XML