| Lipoxygenase-catalyzed formation of R-configuration hydroperoxides. | |
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MedLine Citation:
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PMID: 12432924 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Prototypical lipoxygenases (LOXs) of animals and plants synthesize hydroperoxy fatty acids of the S stereoconfiguration, yet enzymes forming R-configuration products are found in both the animal and plant kingdoms. R-LOX are widespread in aquatic invertebrates, in some of which their R-HETE products have a defined role in reproductive function. A 12R-LOX has been found recently in humans and mice. The human 12R-LOX product, 12R-HETE, appears to be involved in the pathophysiology of psoriasis and other proliferative skin diseases; a role in normal skin development is implied from the spatial and temporal expression patterns of the 12R-LOX in the mouse embryo. In plants, there are few reports of R-LOX activity and in higher plants this is limited to enzymes that catalyze a significant degree of non-specific oxygenation. There are no obvious amino acid sequence motifs characterizing R-LOXs; and in the phylogenetic tree of the LOX superfamily, the R-LOXs do not group into a specific branch of genes. The mechanistic basis of stereocontrol over the oxygenation reaction performed by LOXs may relate to a changed binding orientation of the fatty acid substrate or to the direction of attack by molecular oxygen. A potentially relevant precedent for switching of R- and S-oxygenation specificity was described recently in studies of prostaglandin C-15 oxygenation during cycloxygenase catalysis; single amino acid changes can invert the oxygenation stereospecificity at C-15. In this case, the evidence suggests that R/S switching can occur with the substrate binding in the normal conformation. |
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Authors:
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Claus Schneider; Alan R Brash |
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Publication Detail:
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Type: Journal Article; Research Support, U.S. Gov't, P.H.S.; Review |
Journal Detail:
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Title: Prostaglandins & other lipid mediators Volume: 68-69 ISSN: 1098-8823 ISO Abbreviation: Prostaglandins Other Lipid Mediat. Publication Date: 2002 Aug |
Date Detail:
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Created Date: 2002-11-15 Completed Date: 2003-07-10 Revised Date: 2007-11-14 |
Medline Journal Info:
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Nlm Unique ID: 9808648 Medline TA: Prostaglandins Other Lipid Mediat Country: United States |
Other Details:
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Languages: eng Pagination: 291-301 Citation Subset: IM |
Affiliation:
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Division of Clinical Pharmacology, Vanderbilt University Medical School, Nashville, TN 37232-6602, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Animals Catalysis Humans Hydrogen Peroxide / chemistry*, metabolism* Lipoxygenase / chemistry, classification, metabolism* Models, Molecular Oxygen / metabolism Phylogeny Plant Proteins / metabolism Protein Structure, Tertiary Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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AR-45943/AR/NIAMS NIH HHS; GM-15431/GM/NIGMS NIH HHS; GM-53638/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Plant Proteins; 7722-84-1/Hydrogen Peroxide; 7782-44-7/Oxygen; EC 1.13.11.12/Lipoxygenase |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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