ArticleThe Plant cell2006
The crystal structure of Arabidopsis thaliana allene oxide cyclase: insights into the oxylipin cyclization reaction.
Article in The Plant cell, 2006. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed, 99 citations in OpenAlex.
- Structure and regulation of violaxanthin de-epoxidase, a key enzyme in the photoprotection of photosynthesis.Plant physiology · 2026Review
- Differential Jasmonate Profiles in Oat Roots and Leaves Reveal a Role for 12-Oxo Phytodienoic Acid (OPDA) in Drought Tolerance by Modulating Root Growth.Plants (Basel, Switzerland) · 2026Article
- Octadecanoids as emerging lipid mediators in cnidarian-dinoflagellate symbiosis.Communications biology · 2025Article
- Article
- Tryptophan Stabilization of a Biochemical Carbocation Evaluated by Analysis of π Complexes of 3-Ethylindole with theACS omega · 2023Article
- Stress responsiveness of vindoline accumulation in Catharanthus roseus leaves is mediated through co-expression of allene oxide cyclase with pathway genes.Protoplasma · 2022Article
- Membrane Barrels Are Taller, Fatter, Inside-Out Soluble Barrels.The journal of physical chemistry. B · 2021Article
- Unexpected enzyme-catalysed [4+2] cycloaddition and rearrangement in polyether antibiotic biosynthesis.Nature catalysis · 2019Article
- ALLENE OXIDE SYNTHASE and HYDROPEROXIDE LYASE, Two Non-Canonical Cytochrome P450s inInternational journal of molecular sciences · 2019Review
- Substrate channeling in oxylipin biosynthesis through a protein complex in the plastid envelope of Arabidopsis thaliana.Journal of experimental botany · 2019Article
- Jasmonates: News on Occurrence, Biosynthesis, Metabolism and Action of an Ancient Group of Signaling Compounds.International journal of molecular sciences · 2018Review
- Allene Oxide Synthase Pathway in Cereal Roots: Detection of Novel Oxylipin Graminoxins.ChemistryOpen · 2018Article
- 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
- Physiological and Proteomic Analysis of the Rice MutantFrontiers in plant science · 2017Article
- Dirigent Protein Mode of Action Revealed by the Crystal Structure of AtDIR6.Plant physiology · 2016Article
- Synthesis and Functions of Jasmonates in Maize.Plants (Basel, Switzerland) · 2016Review
- The activity of HYDROPEROXIDE LYASE 1 regulates accumulation of galactolipids containing 12-oxo-phytodienoic acid in Arabidopsis.Journal of experimental botany · 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
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3 authors at 1 institution in 1 country.
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Abstract
We describe the crystallization and structure elucidation of Arabidopsis thaliana allene oxide cyclase 2 (AOC2), a key enzyme in the biosynthesis of jasmonates. In a coupled reaction with allene oxide synthase, AOC2 releases the first cyclic and biologically active metabolite, 12-oxo-phytodienoic acid (OPDA). AOC2 (AT3G25770) folds into an eight-stranded antiparallel beta-barrel with a C-terminal partial helical extension. The protein forms a hydrophobic binding cavity with two distinct polar patches. AOC2 is trimeric in crystals, in vitro and in planta. Based on the observed folding pattern, we assigned AOC2 as a low molecular weight member of the lipocalin family with enzymatic activity in plants. We determined the binding position of the competitive inhibitor vernolic acid (a substrate analog) in the binding pocket. Based on models for bound substrate 12,13-epoxy-9,11,15-octadecatrienoic acid and product OPDA, we propose a reaction scheme that explains the influence of the C15 double bond on reactivity. Reaction is promoted by anchimeric assistance through a conserved Glu residue. The transition state with a pentadienyl carbocation and an oxyanion is stabilized by a strongly bound water molecule and favorable pi-pi interactions with aromatic residues in the cavity. Stereoselectivity results from steric restrictions to the necessary substrate isomerizations imposed by the protein.
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