Document Detail

Action of soybean lipoxygenase 1 on 12-iodo-cis-9-octadecenoic acid and 12-bromo-cis-9-octadecenoic acid.
MedLine Citation:
PMID:  7819206     Owner:  NLM     Status:  MEDLINE    
The ferric form of soybean lipoxygenase catalyzes an elimination reaction on 12-iodo-cis-9-octadecenoic acid (12-IODE) to produce iodide ions and 9,11-octadecadienoic acid (9, 11-ODA). If excess 13(S)-hydroperoxy-cis-9,trans-11-octadecadienoic acid (13-HPOD) is present, the reaction proceeds until about one-half of the racemic 12-IODE is consumed; in the absence of excess 13-HPOD, the reaction stops after about three turnovers. Ferric lipoxygenase also catalyzes the conversion of 12-bromo-cis-9-octadecenoic acid (12-BrODE) to 9,11-ODA at a rate that is less than 25% of that observed with 12-IODE. These elimination reactions cannot be detected with ferrous lipoxygenase or with lipoxygenase that has been inactivated by 5,8,11,14-eicosatetraynoic acid. In the case of 12-IODE, elimination is accompanied by a loss of enzymatic activity; at pH 9.0, about 10 iodide ions are produced per molecule of enzyme inactivated. No inactivation can be detected with 12-BrODE. Ascorbate and hydroxylamine, which can act as free-radical traps, block the inactivation by 12-IODE but do not inhibit the elimination reaction. When the enzyme is inactivated by [1-14C]-12-IODE at pH 9.0, the amount of radioactivity that is covalently bound to the protein is less than 30% of that expected for 1:1 incorporation.(ABSTRACT TRUNCATED AT 250 WORDS)
C H Clapp; A M Grandizio; S A McAskill; R Moser
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Biochemistry     Volume:  34     ISSN:  0006-2960     ISO Abbreviation:  Biochemistry     Publication Date:  1995 Jan 
Date Detail:
Created Date:  1995-02-16     Completed Date:  1995-02-16     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  0370623     Medline TA:  Biochemistry     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  264-72     Citation Subset:  IM    
Department of Chemistry, Bucknell University, Lewisburg, Pennsylvania 17837.
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MeSH Terms
Chromatography, High Pressure Liquid
Free Radical Scavengers / pharmacology
Hydrogen-Ion Concentration
Iodides / metabolism
Linoleic Acids / metabolism
Linoleic Acids, Conjugated*
Lipoxygenase / metabolism*
Lipoxygenase Inhibitors / pharmacology
Oleic Acids / metabolism*,  pharmacology
Soybeans / enzymology*
Grant Support
Reg. No./Substance:
0/12-bromo-9-octadecenoic acid; 0/Free Radical Scavengers; 0/Iodides; 0/Linoleic Acids; 0/Linoleic Acids, Conjugated; 0/Lipoxygenase Inhibitors; 0/Oleic Acids; 116784-49-7/12-iodo-9-octadecenoic acid; 1839-11-8/9,11-linoleic acid; EC

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