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Preparation of omega trideuterated sulfidopeptide leukotrienes: Analysis by FAB/MS
Journal article

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 and Vanderbilt Univ., Nashville, TN (USA)
Prostaglandins, v 37(2), pp 251-258
01 Feb 1989
PMID: 2543036

Abstract

C-20 Trideuterated leukotriene A 4 methyl ester was prepared by Wittig condensation of a deuterated C 9-phosphonium salt with a C 11-epoxydienal. It was then treated separately with glutathione, cysteinylglycine and cysteine. The resulting esters were saponified to give C-20 trideuterated leukotrienes C 4, D 4 and E 4 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 t a wide variety of reagents and reaction conditions. The deuterated leukotrienes will serve as internal standard for the quantitative analysis by mass spectrometry of endogenous sulfidopeptide leukotrienes present in biological fluids.

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Web of Science research areas
Biochemistry & Molecular Biology
Cell Biology
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