Prakash C, Sweetman B J, Sivakumar R, Taffer I M, Zipkin R E, Blair I A
Department of Pharmacology, Vanderbilt University, Nashville, TN 37232.
Prostaglandins. 1989 Feb;37(2):251-8. doi: 10.1016/0090-6980(89)90061-0.
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.
C-20 三氘代白三烯A4甲酯是通过氘代C9-鏻盐与C11-环氧二烯醛的维蒂希缩合反应制备的。然后分别用谷胱甘肽、半胱氨酰甘氨酸和半胱氨酸处理它。将所得酯皂化分别得到C-20三氘代白三烯C4、D4和E4。快原子轰击质谱表明合成化合物含有0.5%至1.0%的氢杂质。在C-20引入氘可确保其对多种试剂和反应条件具有稳定性。氘代白三烯将作为内标，用于通过质谱法定量分析生物流体中存在的内源性硫肽白三烯。
