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Stereochemistry of Hydrogen Removal During Oxygenation of Linoleic Acid by Singlet Oxygen and Synthesis of 11(S)-Deuterium-Labeled Linoleic Acid.
MedLine Citation:
PMID:  21161604     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Exposure of unsaturated fatty acids to singlet oxygen results in the formation of hydroperoxides. In this process, each double bond in the acyl chain produces two regioisomeric hydroperoxides having an (E)-configured double bond. Although such compounds are racemic, the hydrogen removal associated with the oxygenation may, a priori, take place antarafacially, suprafacially or stereorandomly. The present study describes the preparation of [11(S)-(2)H]linoleic acid by two independent methods and the use of this stereospecifically labeled fatty acid to reveal the hidden stereospecificity in singlet oxygenations of polyunsaturated fatty acids. It was found that linoleic acid 9(R)- and 13(S)-hydroperoxides formed from [11(S)-(2)H]linoleic acid both retained the deuterium label whereas the 9(S)- and 13(R)-hydroperoxides were essentially devoid of deuterium. It is concluded that polyunsaturated fatty acid hydroperoxides produced in the presence of singlet oxygen in e.g., plant leaves are formed by a reaction involving addition of oxygen and removal of hydrogen taking place with suprafacial stereochemistry. This result confirms and extends previous mechanistic studies of singlet oxygen-dependent oxygenations.
Authors:
Mats Hamberg
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2010-12-16
Journal Detail:
Title:  Lipids     Volume:  -     ISSN:  1558-9307     ISO Abbreviation:  -     Publication Date:  2010 Dec 
Date Detail:
Created Date:  2010-12-16     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0060450     Medline TA:  Lipids     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Division of Physiological Chemistry II, Department of Medical Biochemistry and Biophysics, Karolinska Institutet, Stockholm, Sweden, Mats.Hamberg@ki.se.
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