ArticleApplied and environmental microbiology2010
Structure, function, and insights into the biosynthesis of a head-to-head hydrocarbon in Shewanella oneidensis strain MR-1.
Article in Applied and environmental microbiology, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
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Who cites it
27 citing papers in PubMed, 91 citations in OpenAlex.
- Shewanella oneidensis: Biotechnological Application of Metal-Reducing Bacteria.Advances in biochemical engineering/biotechnology · 2025Review
- Genomic insights into cryptic cycles of microbial hydrocarbon production and degradation in contiguous freshwater and marine microbiomes.Microbiome · 2023Article
- Screening and Characterization of Next-Generation Biofuels Producing Bacterial Strains.Current microbiology · 2022Article
- Nanoscale battery cathode materials induce DNA damage in bacteria.Chemical science · 2020Article
- Bradymonabacteria, a novel bacterial predator group with versatile survival strategies in saline environments.Microbiome · 2020Article
- Distribution and diversity of olefins and olefin-biosynthesis genes in Gram-positive bacteria.Biotechnology for biofuels · 2020Article
- Linkage of Marine Bacterial Polyunsaturated Fatty Acid and Long-Chain Hydrocarbon Biosynthesis.Frontiers in microbiology · 2019Article
- The role of OleA His285 in orchestration of long-chain acyl-coenzyme A substrates.FEBS letters · 2018Article
- OleA Glu117 is key to condensation of two fatty-acyl coenzyme A substrates in long-chain olefin biosynthesis.The Biochemical journal · 2017Article
- Biobased production of alkanes and alkenes through metabolic engineering of microorganisms.Journal of industrial microbiology & biotechnology · 2017Review
- Active Multienzyme Assemblies for Long-Chain Olefinic Hydrocarbon Biosynthesis.Journal of bacteriology · 2017Article
- Substrate Trapping in Crystals of the Thiolase OleA Identifies Three Channels That Enable Long Chain Olefin Biosynthesis.The Journal of biological chemistry · 2016Article
- Bacterial Long-Chain Polyunsaturated Fatty Acids: Their Biosynthetic Genes, Functions, and Practical Use.Marine drugs · 2016Review
- Biosynthesis of hydrocarbons and volatile organic compounds by fungi: bioengineering potential.Applied microbiology and biotechnology · 2015Review
- On the influence of the culture conditions in bacterial antifouling bioassays and biofilm properties: Shewanella algae, a case study.BMC microbiology · 2014Article
- Fatty Acid-Derived Biofuels and Chemicals Production in Saccharomyces cerevisiae.Frontiers in bioengineering and biotechnology · 2014Review
- Microbial Synthesis of Alka(e)nes.Frontiers in bioengineering and biotechnology · 2013Review
- Crystal structures of Xanthomonas campestris OleA reveal features that promote head-to-head condensation of two long-chain fatty acids.Biochemistry · 2012Article
- Genomic analysis of the hydrocarbon-producing, cellulolytic, endophytic fungus Ascocoryne sarcoides.PLoS genetics · 2012Article
- Engineering Escherichia coli for biodiesel production utilizing a bacterial fatty acid methyltransferase.Applied and environmental microbiology · 2011Article
Corrections and comments
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Authors and funding
6 authors at 3 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
A polyolefinic hydrocarbon was found in nonpolar extracts of Shewanella oneidensis MR-1 and identified as 3,6,9,12,15,19,22,25,28-hentriacontanonaene (compound I) by mass spectrometry, chemical modification, and nuclear magnetic resonance spectroscopy. Compound I was shown to be the product of a head-to-head fatty acid condensation biosynthetic pathway dependent on genes denoted as ole (for olefin biosynthesis). Four ole genes were present in S. oneidensis MR-1. Deletion of the entire oleABCD gene cluster led to the complete absence of nonpolar extractable products. Deletion of the oleC gene alone generated a strain that lacked compound I but produced a structurally analogous ketone. Complementation of the oleC gene eliminated formation of the ketone and restored the biosynthesis of compound I. A recombinant S. oneidensis strain containing oleA from Stenotrophomonas maltophilia strain R551-3 produced at least 17 related long-chain compounds in addition to compound I, 13 of which were identified as ketones. A potential role for OleA in head-to-head condensation was proposed. It was further proposed that long-chain polyunsaturated compounds aid in adapting cells to a rapid drop in temperature, based on three observations. In S. oneidensis wild-type cells, the cellular concentration of polyunsaturated compounds increased significantly with decreasing growth temperature. Second, the oleABCD deletion strain showed a significantly longer lag phase than the wild-type strain when shifted to a lower temperature. Lastly, compound I has been identified in a significant number of bacteria isolated from cold environments.
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