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Chem Phys Lipids ; 130(2): 117-26, 2004 Jul.
Article in English | MEDLINE | ID: mdl-15172828

ABSTRACT

Total synthesis of (5Z,8Z,11Z,14Z)-18- and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their [5,6,8,9,11,12,14,15-3H8]-analogues via the corresponding p-toluenesulphonates is reported. This synthetic approach allows the preparation of radioactively labelled arachidonic acid derivatives following a common synthetic route. Activity assays indicated that 15-lipoxygenases may tolerate the azido group in the substrate binding pocket and thus, radioactively labelled azido compounds may be used as photo-affinity probes to investigate mechanistic features of eicosanoid biosynthesis.


Subject(s)
Arachidonic Acid/chemistry , Arachidonic Acid/chemical synthesis , Animals , Arachidonate 15-Lipoxygenase/metabolism , Arachidonic Acid/metabolism , Kinetics , Molecular Structure , Oxidation-Reduction , Rabbits , Reticulocytes/enzymology , Glycine max/enzymology
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