Document Detail


Enantiomeric separation and analysis of unsaturated hydroperoxy fatty acids by chiral column chromatography-mass spectrometry.
MedLine Citation:
PMID:  18667369     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Hydroperoxides of 18:2n-6 and 20:4n-6 were obtained by autoxidation and photooxidation. The enantiomers were separated as free acids (Reprosil Chiral-NR column, eluted with hexane containing 1-1.2% alcoholic modifier) and analyzed by on line UV detection (234 nm) and liquid chromatography-MS/MS/MS of carboxylate anions (A(-)-->(A(-)-18)-->full scan) in an ion trap. The combination of UV and MS/MS/MS analysis facilitated identification of hydroperoxides even in complex mixtures of autoxidized or photooxidized fatty acids. The signal intensities increased about two orders of magnitude by raising the isolation width of A(-) from 1.5 amu to 5 or 10 amu for cis-trans conjugated hydroperoxy fatty acids, and one order of magnitude or more for non-conjugated hydroperoxy fatty acids. The S enantiomer of 8-, 9-, 10-, and 13-hydroperoxyoctadecadienoic acids and the S enantiomer of cis-trans conjugated hydroperoxyeicosatetraenoic acids eluted before the corresponding R enantiomer with two exceptions (11-hydroperoxylinoleic acid and 8-hydroperoxyeicosa-5Z,9E,11Z,14Z-tetraenoic acid). The separation of enantiomers or regioisomers could be improved by the choice of either isopropanol or methanol as alcoholic modifier.
Authors:
Ulrike Garscha; Tomas Nilsson; Ernst H Oliw
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-07-18
Journal Detail:
Title:  Journal of chromatography. B, Analytical technologies in the biomedical and life sciences     Volume:  872     ISSN:  1570-0232     ISO Abbreviation:  J. Chromatogr. B Analyt. Technol. Biomed. Life Sci.     Publication Date:  2008 Sep 
Date Detail:
Created Date:  2008-08-26     Completed Date:  2008-10-28     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101139554     Medline TA:  J Chromatogr B Analyt Technol Biomed Life Sci     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  90-8     Citation Subset:  IM    
Affiliation:
Section of Biochemical Pharmacology, Department of Pharmaceutical Biosciences, Biomedical Center, Uppsala University, SE-751 24 Uppsala, Sweden.
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MeSH Terms
Descriptor/Qualifier:
Chromatography, High Pressure Liquid / methods*
Fatty Acids, Unsaturated / analysis,  isolation & purification*
Spectrophotometry, Ultraviolet
Stereoisomerism
Tandem Mass Spectrometry
Chemical
Reg. No./Substance:
0/Fatty Acids, Unsaturated

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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