Document Detail

Lipoxygenase-catalyzed formation of R-configuration hydroperoxides.
MedLine Citation:
PMID:  12432924     Owner:  NLM     Status:  MEDLINE    
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.
Claus Schneider; Alan R Brash
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.; Review    
Journal Detail:
Title:  Prostaglandins & other lipid mediators     Volume:  68-69     ISSN:  1098-8823     ISO Abbreviation:  Prostaglandins Other Lipid Mediat.     Publication Date:  2002 Aug 
Date Detail:
Created Date:  2002-11-15     Completed Date:  2003-07-10     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  9808648     Medline TA:  Prostaglandins Other Lipid Mediat     Country:  United States    
Other Details:
Languages:  eng     Pagination:  291-301     Citation Subset:  IM    
Division of Clinical Pharmacology, Vanderbilt University Medical School, Nashville, TN 37232-6602, USA.
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MeSH Terms
Hydrogen Peroxide / chemistry*,  metabolism*
Lipoxygenase / chemistry,  classification,  metabolism*
Models, Molecular
Oxygen / metabolism
Plant Proteins / metabolism
Protein Structure, Tertiary
Grant Support
Reg. No./Substance:
0/Plant Proteins; 7722-84-1/Hydrogen Peroxide; 7782-44-7/Oxygen; EC

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