Synthesis of [14,15,17,17,18,18‐²H₆]‐leukotriene B₄

Abstract

Incubation of [ 14,15,17,17,18,18-2H(j] leukotriene A4 obtained by hydrolysis of chiral [14,15,17,17,18,18-2H6] leukotriene A 4 methylester with human monocytes resulted in the formation of [ 14,15,17,17,18,18-2H6] leukotriene B4 (dg-LTB4) and its trans isomers 6-trans-db-LTBq and 12-epi-6-trans-d6-LTB4 in high isotopic purity (99.4 % 2H). dg-LTB4 was separated from its trans-isomers by reversedphase high-performance liquid chromatography and identified by gas chromatography mass spectrometry. d(j-LTB4 is shown to be a useful internal standard for gas chromatographic mass spectrometric analysis of LTB4 in biological matrix.