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 through a common synthetic route.
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.
Romanov
Stepan G
SG
M.V. Lomonosov State Academy of Fine Chemical Technology, Moscow, Russia.
Ivanov
Igor V
IV
Shevchenko
Valery P
VP
Nagaev
Igor Yu
IY
Pushkov
Alexandr A
AA
Myasoedov
Nikolai F
NF
Myagkova
Galina I
GI
Kuhn
Hartmut
H
D000818:Animals; D001093:Arachidonate 15-Lipoxygenase / Q000378:metabolism; D016718:Arachidonic Acid / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D007700:Kinetics; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011817:Rabbits; D012156:Reticulocytes / Q000201:enzymology; D013025:Glycine max / Q000201:enzymology
D016718:Arachidonic Acid; D001093:Arachidonate 15-Lipoxygenase