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Methyl Esterification of Fatty Acids and Prostaglandins with Trimethylsilyl diazomethane
Author(s) -
Sengupta Aditi Munmun,
Basu Hemendra N.,
Pernecky Steven
Publication year - 2007
Publication title -
the faseb journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.709
H-Index - 277
eISSN - 1530-6860
pISSN - 0892-6638
DOI - 10.1096/fasebj.21.5.a605-a
Subject(s) - diazomethane , chemistry , polyunsaturated fatty acid , trimethylsilyl , organic chemistry , arachidonic acid , fatty acid , linoleic acid , chromatography , enzyme
A variety of GC‐MS and LC‐MS methods have been developed to resolve and quantify fatty acids and oxidation products of the polyunsaturated fatty acids, including those of arachidonic acid such as the prostaglandins. A novel method for formation of methyl esters that uses the reagent trimethylsilyl diazomethane (TMSD) has been developed for fatty acids and eicosanoids, and, unlike some reagents, such as diazomethane, TMSD is safe and easy to use. This method gives a good yield of methyl esters for the fatty acids linoleic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid, and docosahexaenoic acid, as well as for the oxidation products of fatty acids mainly the prostanoids. In these experiments, heptadecanoic acid is used as the internal standard. This methylation method with TMSD is also used to characterize the constituent fatty acids of phospholipids. Standard calibration curves constructed for the fatty acid methyl esters and prostaglandins, namely PGE2 and PGF2α, shows linearity in the range of 10 to 900 pg/ml with the deuterated compounds of prostaglandins as the internal standard. Comparison of methyl esterification reactions using TMSD, diazomethane, or tetramethyl ammonium hydroxide in methanol with subsequent analysis by GC‐ MS reveals that methylation esterification with TMSD to be a promising and reliable approach in routine analysis of fatty acids and prostanoids in clinical chemistry.