Preparation of omega trideuterated sulfidopeptide leukotrienes: analysis by FAB/MS.
C-20 Trideuterated leukotriene A4 methyl ester was prepared by Wittig condensation of a deuterated C9-phosphonium salt with a C11-epoxydienal. It was then treated separately with glutathione, cysteinylglycine and cysteine. The resulting esters were saponified to give C-20 trideuterated leukotrienes C4, D4 and E4 respectively. Fast atom bombardment mass spectrometry showed that the synthetic compounds contained from 0.5 to 1.0% protium impurity. Introduction of deuterium at C-20 ensures that it is stable to a wide variety of reagents and reaction conditions. The deuterated leukotrienes will serve as internal standards for the quantitative analysis by mass spectrometry of endogenous sulfidopeptide leukotrienes present in biological fluids.
Prakash
C
C
Department of Pharmacology, Vanderbilt University, Nashville, TN 37232.
Sweetman
B J
BJ
Sivakumar
R
R
Taffer
I M
IM
Zipkin
R E
RE
Blair
I A
IA
D003903:Deuterium; D007553:Isotope Labeling; D017572:Leukotriene A4 / Q000031:analogs & derivatives*; D017999:Leukotriene E4; D015289:Leukotrienes / Q000032:analysis*; D013058:Mass Spectrometry / Q000379:methods; D013189:SRS-A / Q000031:analogs & derivatives / Q000032:analysis
D017572:Leukotriene A4; D015289:Leukotrienes; D013189:SRS-A; D017999:Leukotriene E4; C043073:leukotriene A methyl ester; D003903:Deuterium