ArticleLipids1999
On the specificity of allene oxide cyclase.
Article in Lipids, 1999. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 57 citations in OpenAlex.
- Ligand diversity contributes to the full activation of the jasmonate pathway inProceedings of the National Academy of Sciences of the United States of America · 2022Article
- Biochemical Characterization of 13-Lipoxygenases ofInternational journal of molecular sciences · 2021Article
- Detection of the First Epoxyalcohol Synthase/Allene Oxide Synthase (CYP74 Clan) in the Lancelet (International journal of molecular sciences · 2021Article
- Allene Oxide Synthase Pathway in Cereal Roots: Detection of Novel Oxylipin Graminoxins.ChemistryOpen · 2018Article
- Synthesis and Functions of Jasmonates in Maize.Plants (Basel, Switzerland) · 2016Review
- Activity Regulation by Heteromerization of Arabidopsis Allene Oxide Cyclase Family Members.Plants (Basel, Switzerland) · 2016Article
- Jasmonates act positively in adventitious root formation in petunia cuttings.BMC plant biology · 2015Article
- Crystal structures of Physcomitrella patens AOC1 and AOC2: insights into the enzyme mechanism and differences in substrate specificity.Plant physiology · 2012Article
- Evidence for an ionic intermediate in the transformation of fatty acid hydroperoxide by a catalase-related allene oxide synthase from the Cyanobacterium Acaryochloris marina.The Journal of biological chemistry · 2009Article
- The crystal structure of Arabidopsis thaliana allene oxide cyclase: insights into the oxylipin cyclization reaction.The Plant cell · 2006Article
- Suppression of allene oxide cyclase in hairy roots of Medicago truncatula reduces jasmonate levels and the degree of mycorrhization with Glomus intraradices.Plant physiology · 2005Article
- Jasmonate biosynthesis and the allene oxide cyclase family of Arabidopsis thaliana.Plant molecular biology · 2003Article
- The lipoxygenase pathway in tulip (Tulipa gesneriana): detection of the ketol route.The Biochemical journal · 2000Article
- Octadecanoid-derived alteration of gene expression and the "oxylipin signature" in stressed barley leaves. Implications for different signaling pathways.Plant physiology · 2000Article
- Article
Corrections and comments
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Authors and funding
3 authors at 3 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Jasmonic acid is a carbocyclic fatty acid that is biosynthesized from alpha-linolenic acid in several steps. The formation of the ring structure of jasmonic acid is catalyzed by the enzyme allene oxide cyclase (EC 5.3.99.6) and involves the cyclization of an unstable allene oxide into the cyclopentenone 12-oxo-10,15(Z)-phytodienoic acid. In this study, a number of allene oxides were generated, and their enzymatic and nonenzymatic cyclization into cyclopentenones was investigated. Nonenzymatic cyclization was observed with allene oxides having one pair of conjugated double bonds and an additional isolated double bond in the beta,gamma position relative to the epoxide group, i.e., the partial structure 4,5-epoxy-1,3,7-octatriene. Enzymatic cyclization took place provided that this structural element was inserted in the fatty acid chain with its epoxide group in the n-6,7 position and the isolated double bond in the n-3 position. A number of oxygenated fatty acids having structural features in common with the natural allene oxides were tested as inhibitors of allene oxide cyclase. Fatty acids having an allene oxide structure in the n-6,7 position but lacking the double bond in the n-3 position, as well as fatty acids having a saturated epoxide group in the n-6,7 position, served as competitive inhibitors of the enzyme. Data on the substrate specificity of allene oxide synthase (EC 4.2.1.92) from corn seeds indicated that fatty acid hydroperoxides with a double bond at n-3 and with the hydroperoxide function at n-6 exhibit the highest affinity but the slowest reaction velocity.
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Registered trials
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.