Document Detail


Vicinal hydroxylation of unsaturated fatty acids for structural characterization of intact neutral phospholipids by negative electrospray ionization tandem quadrupole mass spectrometry.
MedLine Citation:
PMID:  15317043     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
We report a novel method allowing the complete structural characterization of intact species of the phospholipid classes phosphatidylcholine and phosphatidylethanolamine by utilizing negative electrospray ionization quadrupole tandem mass spectrometry (MS/MS). Information on the molecular weight of the intact phospholipid species, the class to which it belongs, the molecular mass of the fatty acid substituents and their regioisomerism, is easily revealed by MS/MS. Throughout our investigations the R2COO- ions were more abundant than the R1COO- ions, and this observation is used for regioisomeric assignment of the two fatty acids. However, for phospholipid species containing an unsaturated fatty acid, information on the position of the double bond is not achieved in this way. By converting the olefinic sites to their 1,2-dihydroxylated derivatives, information on the position of the hydroxyl groups (and hence of the double bond) is obtained by performing a second MS/MS experiment. Thus, a complete structural characterization of intact phosphatidylcholine and phosphatidylethanolamine species is obtained by performing these two MS/MS experiments. In order to ensure structural distinction of isobaric species, a number of phosphatidylethanolamine and phosphatidylcholine species were synthesized from lyso-phosphatidylcholine and analyzed by the present method. The applicability of the method to real samples is also demonstrated by the complete structural elucidation of the two phosphatidylcholine species 16:0/18:1Delta9 and 16:0/18:1Delta11 from egg yolk.
Authors:
Morten K Moe; Trude Anderssen; Morten B Strøm; Einar Jensen
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Publication Detail:
Type:  Comparative Study; Evaluation Studies; Journal Article; Research Support, Non-U.S. Gov't; Validation Studies    
Journal Detail:
Title:  Rapid communications in mass spectrometry : RCM     Volume:  18     ISSN:  0951-4198     ISO Abbreviation:  Rapid Commun. Mass Spectrom.     Publication Date:  2004  
Date Detail:
Created Date:  2004-09-20     Completed Date:  2004-11-09     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8802365     Medline TA:  Rapid Commun Mass Spectrom     Country:  England    
Other Details:
Languages:  eng     Pagination:  2121-30     Citation Subset:  IM    
Copyright Information:
Copyright 2004 John Wiley & Sons, Ltd.
Affiliation:
Institute of Pharmacy, University of Tromsø, N-9037 Tromsø, Norway. mortenm@farmasi.uit.no
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MeSH Terms
Descriptor/Qualifier:
Egg Yolk / chemistry
Fatty Acids, Unsaturated / analysis*,  chemistry*
Hydroxylation
Ions
Isomerism
Molecular Structure
Molecular Weight
Phosphatidylcholines / analysis*,  chemistry*
Phosphatidylethanolamines / analysis*,  chemistry*
Phospholipids / analysis,  chemistry
Spectrometry, Mass, Electrospray Ionization / methods*
Chemical
Reg. No./Substance:
0/Fatty Acids, Unsaturated; 0/Ions; 0/Phosphatidylcholines; 0/Phosphatidylethanolamines; 0/Phospholipids; 39382-08-6/phosphatidylethanolamine

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


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