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A bacterial biosynthetic pathway for methylated furan fatty acids

Authors
  • Lemke, Rachelle A. S.1, 2, 3
  • Olson, Stephanie M.1, 2, 3
  • Morse, Kaitlin2, 3
  • Karlen, Steven D.2, 3, 4
  • Higbee, Alan2, 3, 5
  • Beebe, Emily T.3
  • Ralph, John2, 3, 4
  • Coon, Joshua J.3, 5, 6
  • Fox, Brian G.2, 3, 4
  • Donohue, Timothy J.1, 2, 3
  • 1 Department of Bacteriology, University of Wisconsin, Madison, Wisconsin, USA
  • 2 Wisconsin Energy Institute, University of Wisconsin, Madison, Wisconsin, USA
  • 3 Great Lakes Bioenergy Research Center, University of Wisconsin, Madison, Wisconsin, USA
  • 4 Department of Biochemistry, University of Wisconsin, Madison, Wisconsin, USA
  • 5 Genome Center of Wisconsin, University of Wisconsin, Madison, Wisconsin, USA
  • 6 Department of Biomolecular Chemistry, University of Wisconsin, Madison, Wisconsin, USA
Type
Published Article
Journal
Journal of Biological Chemistry
Publisher
American Society for Biochemistry and Molecular Biology
Publication Date
May 20, 2020
Volume
295
Issue
29
Pages
9786–9801
Identifiers
DOI: 10.1074/jbc.RA120.013697
PMID: 32434926
PMCID: PMC7380195
Source
PubMed Central
Keywords
License
Green

Abstract

Fatty acids play many important roles in cells and also in industrial processes. Furan fatty acids (FuFAs) are present in the lipids of some plant, fish, and microbial species and appear to function as second messengers in pathways that protect cells from membrane-damaging agents. We report here the results of chemical, genetic, and synthetic biology experiments to decipher the biosynthesis of the monomethylated FuFA, methyl 9-(3-methyl-5-pentylfuran-2-yl) nonanoate (9M5-FuFA), and its dimethyl counterpart, methyl 9-(3,4-dimethyl-5-pentylfuran-2-yl) nonanoate (9D5-FuFA), in two α-proteobacteria. Each of the steps in FuFA biosynthesis occurs on pre-existing phospholipid fatty acid chains, and we identified pathway intermediates and the gene products that catalyze 9M5-FuFA and 9D5-FuFA synthesis in Rhodobacter sphaeroides 2.4.1 and Rhodopseudomonas palustris CGA009. One previously unknown pathway intermediate was a methylated diunsaturated fatty acid, (10 E, 12 E )-11-methyloctadeca-10,12-dienoic acid (11Me-10 t ,12 t -18:2), produced from (11 E )-methyloctadeca-11-enoic acid (11Me-12 t -18:1) by a newly identified fatty acid desaturase, UfaD. We also show that molecular oxygen (O2) is the source of the oxygen atom in the furan ring of 9M5-FuFA, and our findings predict that an O2-derived oxygen atom is incorporated into 9M5-FuFA via a protein, UfaO, that uses the 11Me-10 t, 12 t -18:2 fatty acid phospholipid chain as a substrate. We discovered that R. palustris also contains a SAM-dependent methylase, FufM, that produces 9D5-FuFA from 9M5-FuFA. These results uncover the biochemical sequence of intermediates in a bacterial pathway for 9M5-FuFA and 9D5-FuFA biosynthesis and suggest the existence of homologs of the enzymes identified here that could function in FuFA biosynthesis in other organisms.

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