ArticleProceedings of the National Academy of Sciences of the United States of America2007
Enzymatic synthesis of a bicyclobutane fatty acid by a hemoprotein lipoxygenase fusion protein from the cyanobacterium Anabaena PCC 7120.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2007. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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28 citing papers in PubMed, 63 citations in OpenAlex.
- Intricate Evolution of Multifunctional Lipoxygenase in Red Algae.International journal of molecular sciences · 2024Article
- Synthesis and Applications of Bicyclo[1.1.0]butyl and Azabicyclo[1.1.0]butyl Organometallics.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Review
- Bicyclobutanes: from curiosities to versatile reagents and covalent warheads.Chemical science · 2022Review
- One-Pot Synthesis of Strain-Release Reagents from Methyl Sulfones.Journal of the American Chemical Society · 2022Article
- Recent developments in chemical conjugation strategies targeting native amino acids in proteins and their applications in antibody-drug conjugates.Chemical science · 2021Review
- Synthesis of 1,3-disubstituted bicyclo[1.1.0]butanesChemical science · 2021Article
- ALLENE OXIDE SYNTHASE and HYDROPEROXIDE LYASE, Two Non-Canonical Cytochrome P450s inInternational journal of molecular sciences · 2019Review
- Formation and Cleavage of C-C Bonds by Enzymatic Oxidation-Reduction Reactions.Chemical reviews · 2018Review
- Enzymatic construction of highly strained carbocycles.Science (New York, N.Y.) · 2018Article
- Oxygen Activation and Radical Transformations in Heme Proteins and Metalloporphyrins.Chemical reviews · 2018Review
- Catalase-Related Allene Oxide Synthase, on a Biosynthetic Route to Fatty Acid Cyclopentenones: Expression and Assay of the Enzyme and Preparation of the 8R-HPETE Substrate.Methods in enzymology · 2018Article
- A fungal catalase reacts selectively with the 13S fatty acid hydroperoxide products of the adjacent lipoxygenase gene and exhibits 13S-hydroperoxide-dependent peroxidase activity.Biochimica et biophysica acta. Molecular and cell biology of lipids · 2017Article
- The Thr-His Connection on the Distal Heme of Catalase-Related Hemoproteins: A Hallmark of Reaction with Fatty Acid Hydroperoxides.Chembiochem : a European journal of chemical biology · 2016Review
- Crystal structure of a lipoxygenase from Cyanothece sp. may reveal novel features for substrate acquisition.Journal of lipid research · 2016Article
- Article
- Inhibitory effects of a novel Val to Thr mutation on the distal heme of human catalase.Biochimie · 2014Article
- An ancient relative of cyclooxygenase in cyanobacteria is a linoleate 10S-dioxygenase that works in tandem with a catalase-related protein with specific 10S-hydroperoxide lyase activity.The Journal of biological chemistry · 2014Article
- Hydrogen tunneling in a prokaryotic lipoxygenase.Biochemistry · 2014Article
- Biosynthesis, isolation, and NMR analysis of leukotriene A epoxides: substrate chirality as a determinant of the cis or trans epoxide configuration.Journal of lipid research · 2013Article
- Cytochrome P450-type hydroxylation and epoxidation in a tyrosine-liganded hemoprotein, catalase-related allene oxide synthase.The Journal of biological chemistry · 2012Article
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7 authors at 1 institution in 1 country.
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Abstract
Biological transformations of polyunsaturated fatty acids often lead to chemically unstable products, such as the prostaglandin endoperoxides and leukotriene A(4) epoxide of mammalian biology and the allene epoxides of plants. Here, we report on the enzymatic production of a fatty acid containing a highly strained bicyclic four-carbon ring, a moiety known previously only as a model compound for mechanistic studies in chemistry. Starting from linolenic acid (C18.3omega3), a dual function protein from the cyanobacterium Anabaena PCC 7120 forms 9R-hydroperoxy-C18.3omega3 in a lipoxygenase domain, then a catalase-related domain converts the 9R-hydroperoxide to two unstable allylic epoxides. We isolated and identified the major product as 9R,10R-epoxy-11trans-C18.1 containing a bicyclo[1.1.0]butyl ring on carbons 13-16, and the minor product as 9R,10R-epoxy-11trans,13trans,15cis-C18.omega3, an epoxide of the leukotriene A type. Synthesis of both epoxides can be understood by initial transformation of the hydroperoxide to an epoxy allylic carbocation. Rearrangement to an intermediate bicyclobutonium ion followed by deprotonation gives the bicyclobutane fatty acid. This enzymatic reaction has no parallel in aqueous or organic solvent, where ring-opened cyclopropanes, cyclobutanes, and homoallyl products are formed. Given the capability shown here for enzymatic formation of the highly strained and unstable bicyclobutane, our findings suggest that other transformations involving carbocation rearrangement, in both chemistry and biology, should be examined for the production of the high energy bicyclobutanes.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.