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)

Full Text: HTML

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.

Related Compounds

  • (-)-LEUKOTRIE...

Related Articles:

Transcellular metabolism of neutrophil-derived leukotriene A4 by human platelets. A potential cellular source of leukotriene C4.

1988-01-05

[J. Biol. Chem. 263 , 174, (1988)]

Transformation of leukotriene A4 methyl ester to leukotriene C4 monomethyl ester by cytosolic rat glutathione transferases.

1984-10-01

[FEBS Lett. 175(2) , 289-93, (1984)]

Leukotriene C synthase in mouse mastocytoma cells. An enzyme distinct from cytosolic and microsomal glutathione transferases.

1988-03-15

[Biochem. J. 250(3) , 713-8, (1988)]

Glutathione S-transferase-dependent conjugation of leukotriene A4-methyl ester to leukotriene C4-methyl ester in mammalian skin.

1992-11-17

[Biochem. Pharmacol. 44 , 2047-2053, (1992)]

Irreversible inactivation of 5-lipoxygenase by leukotriene A4. Characterization of product inactivation with purified enzyme and intact leukocytes.

1994-01-28

[J. Biol. Chem. 269(4) , 2627-31, (1994)]

More Articles...