ArticleThe Journal of biological chemistry2011
Purification and characterization of OleA from Xanthomonas campestris and demonstration of a non-decarboxylative Claisen condensation reaction.
Article in The Journal of biological chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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22 citing papers in PubMed, 64 citations in OpenAlex.
- Biosynthesis of the Unusual Carbon Skeleton of Nocuolin A.ACS chemical biology · 2022Article
- Microbial engineering to produce fatty alcohols and alkanes.Journal of industrial microbiology & biotechnology · 2021Review
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- Undecane production by cold-adapted bacteria from Antarctica.Extremophiles : life under extreme conditions · 2020Article
- Global analysis of adenylate-forming enzymes reveals β-lactone biosynthesis pathway in pathogenicThe Journal of biological chemistry · 2020Article
- Metabolic engineering of β-oxidation to leverage thioesterases for production of 2-heptanone, 2-nonanone and 2-undecanone.Metabolic engineering · 2020Article
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- 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
- β-Lactone Synthetase Found in the Olefin Biosynthesis Pathway.Biochemistry · 2017Article
- Substrate Trapping in Crystals of the Thiolase OleA Identifies Three Channels That Enable Long Chain Olefin Biosynthesis.The Journal of biological chemistry · 2016Article
- Fatty Acid-Derived Biofuels and Chemicals Production in Saccharomyces cerevisiae.Frontiers in bioengineering and biotechnology · 2014Review
- Microbial production of fatty acid-derived fuels and chemicals.Current opinion in biotechnology · 2013Review
- Microbial Synthesis of Alka(e)nes.Frontiers in bioengineering and biotechnology · 2013Review
- An insect-specific P450 oxidative decarbonylase for cuticular hydrocarbon biosynthesis.Proceedings of the National Academy of Sciences of the United States of America · 2012Article
- Crystal structures of Xanthomonas campestris OleA reveal features that promote head-to-head condensation of two long-chain fatty acids.Biochemistry · 2012Article
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4 authors at 2 institutions in 1 country.
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No grant is acknowledged in the PubMed record.
Abstract
OleA catalyzes the condensation of fatty acyl groups in the first step of bacterial long-chain olefin biosynthesis, but the mechanism of the condensation reaction is controversial. In this study, OleA from Xanthomonas campestris was expressed in Escherichia coli and purified to homogeneity. The purified protein was shown to be active with fatty acyl-CoA substrates that ranged from C(8) to C(16) in length. With limiting myristoyl-CoA (C(14)), 1 mol of the free coenzyme A was released/mol of myristoyl-CoA consumed. Using [(14)C]myristoyl-CoA, the other products were identified as myristic acid, 2-myristoylmyristic acid, and 14-heptacosanone. 2-Myristoylmyristic acid was indicated to be the physiologically relevant product of OleA in several ways. First, 2-myristoylmyristic acid was the major condensed product in short incubations, but over time, it decreased with the concomitant increase of 14-heptacosanone. Second, synthetic 2-myristoylmyristic acid showed similar decarboxylation kinetics in the absence of OleA. Third, 2-myristoylmyristic acid was shown to be reactive with purified OleC and OleD to generate the olefin 14-heptacosene, a product seen in previous in vivo studies. The decarboxylation product, 14-heptacosanone, did not react with OleC and OleD to produce any demonstrable product. Substantial hydrolysis of fatty acyl-CoA substrates to the corresponding fatty acids was observed, but it is currently unclear if this occurs in vivo. In total, these data are consistent with OleA catalyzing a non-decarboxylative Claisen condensation reaction in the first step of the olefin biosynthetic pathway previously found to be present in at least 70 different bacterial strains.
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