ArticlePlant physiology2012
Crystal structures of Physcomitrella patens AOC1 and AOC2: insights into the enzyme mechanism and differences in substrate specificity.
Article in Plant physiology, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 39 citations in OpenAlex.
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- A multiplant transcriptomic atlas reveals conserved and lineage-specific defense architectures in response toProceedings of the National Academy of Sciences of the United States of America · 2026Article
- Excessive DAO inhibits myoblast migration, leading to impaired myotube fusion and muscle strength decline by reducing ECM.Frontiers in bioengineering and biotechnology · 2025Article
- Antibiofilm and Antivirulence Activities of Gold and Zinc Oxide Nanoparticles Synthesized from Kimchi-IsolatedAntibiotics (Basel, Switzerland) · 2022Article
- Design and optimization of enzymatic activity in a de novo β-barrel scaffold.Protein science : a publication of the Protein Society · 2022Article
- A non-targeted metabolomics analysis identifies wound-induced oxylipins inFrontiers in plant science · 2022Article
- Transcriptome Analysis of Rat Lungs Exposed to Moxa Smoke after Acute Toxicity Testing.Evidence-based complementary and alternative medicine : eCAM · 2021Article
- Membrane Lipids, Waxes and Oxylipins in the Moss Model Organism Physcomitrella patens.Plant & cell physiology · 2019Review
- Jasmonates: News on Occurrence, Biosynthesis, Metabolism and Action of an Ancient Group of Signaling Compounds.International journal of molecular sciences · 2018Review
- Structural Evidence for the Substrate Channeling of Rice Allene Oxide Cyclase in Biologically Analogous Nazarov Reaction.Frontiers in chemistry · 2018Article
- 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
- Dirigent Protein Mode of Action Revealed by the Crystal Structure of AtDIR6.Plant physiology · 2016Article
- Investigation into 9(S)-HPODE-derived allene oxide to cyclopentenone cyclization mechanism via diradical oxyallyl intermediates.Organic & biomolecular chemistry · 2016Article
- Activity Regulation by Heteromerization of Arabidopsis Allene Oxide Cyclase Family Members.Plants (Basel, Switzerland) · 2016Article
- Trimeric structure of (+)-pinoresinol-forming dirigent protein at 1.95 Å resolution with three isolated active sites.The Journal of biological chemistry · 2015Article
- Oxylipins in moss development and defense.Frontiers in plant science · 2015Review
- Jasmonates: biosynthesis, perception, signal transduction and action in plant stress response, growth and development. An update to the 2007 review in Annals of Botany.Annals of botany · 2013Review
- Activation of Defense Mechanisms against Pathogens in Mosses and Flowering Plants.International journal of molecular sciences · 2013Article
- Biosynthesis of allene oxides in Physcomitrella patens.BMC plant biology · 2012Article
Corrections and comments
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Authors and funding
10 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
In plants, oxylipins regulate developmental processes and defense responses. The first specific step in the biosynthesis of the cyclopentanone class of oxylipins is catalyzed by allene oxide cyclase (AOC) that forms cis(+)-12-oxo-phytodienoic acid. The moss Physcomitrella patens has two AOCs (PpAOC1 and PpAOC2) with different substrate specificities for C₁₈- and C₂₀-derived substrates, respectively. To better understand AOC's catalytic mechanism and to elucidate the structural properties that explain the differences in substrate specificity, we solved and analyzed the crystal structures of 36 monomers of both apo and ligand complexes of PpAOC1 and PpAOC2. From these data, we propose the following intermediates in AOC catalysis: (1) a resting state of the apo enzyme with a closed conformation, (2) a first shallow binding mode, followed by (3) a tight binding of the substrate accompanied by conformational changes in the binding pocket, and (4) initiation of the catalytic cycle by opening of the epoxide ring. As expected, the substrate dihydro analog cis-12,13S-epoxy-9Z,15Z-octadecadienoic acid did not cyclize in the presence of PpAOC1; however, when bound to the enzyme, it underwent isomerization into the corresponding trans-epoxide. By comparing complex structures of the C₁₈ substrate analog with in silico modeling of the C₂₀ substrate analog bound to the enzyme allowed us to identify three major molecular determinants responsible for the different substrate specificities (i.e. larger active site diameter, an elongated cavity of PpAOC2, and two nonidentical residues at the entrance of the active site).
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