Prostaglandins 1989-02-01

Preparation of omega trideuterated sulfidopeptide leukotrienes: analysis by FAB/MS.

C Prakash, B J Sweetman, R Sivakumar, I M Taffer, R E Zipkin, I A Blair

Index: Prostaglandins 37(2) , 251-8, (1989)

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Abstract

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.